Antioxidants Properties of Spices

360 32 Juniper Antioxidant Properties Methanol extracts of juniper berries had high antioxidant activities as determined by the DPPH test, reducing power assay and TBA assay (Miceli et al. 2009). A positive correlation was found between the primary antioxidant activity and total phenolic content in different Juniper species (Taviano et al. 2011). Different extracts of leaves, ripe fruits, and unripe fruits of Juniperus species, including J. communis, were studied for the anticholinesterase and antioxidant activity by the ferrous ion- chelating, superoxide radical scavenging, and ferric-reducing antioxidant power (FRAP) assays. Total phenol and flavonoid contents of the extracts were also deter- mined. They all showed good antioxidant activity, but the leaf extracts usually had higher antioxidant activity (Orhan et al. 2011). Regulatory Status GRAS 182.20. Standard ISO 7377 (Specification), ISO 8897 (Oil of juniper berry). References Acuna UM, Atha DE, Ma J, Nee MH, Kennelly EJ (2002) Antioxidant capacities of ten edible North American plants. Phytother Res 16(1):63–65 Al-Mustafa AH, Al-Thunibat OY (2008) Antioxidant activity of some Jordanian medicinal plants used traditionally for treatment of diabetes. Pak J Biol Sci 11(3):351–358 Angioni A, Barra A, Russo MT, Coroneo V, Dessi S, Cabras P (2003) Chemical composition of the essential oils of Juniperus from ripe and unripe berries and leaves and their antimicrobial activ- ity. J Agric Food Chem 51(10):3073–3078 Burits M, Asres K, Bucar F (2001) The antioxidant activity of the essential oils of Artemisia afra, Artemisia abyssinica and Juniperus procera. Phytother Res 15(2):103–108 Carroll JF, Tabanca N, Kramer M, Elejalde NM, Wedge DE, Bernier UR, Coy M, Becnel JJ, Demirci B, Baser KH, Zhang J, Zhang S (2011) Essential oils of Cupressus funebris, Juniperus communis, and J. chinensis (Cupressaceae) as repellents against ticks (Acari: Ixodidae) and mosquitoes (Diptera: Culicidae) and as toxicants against mosquitoes. J Vector Ecol 36(2):258–268 De Marino S, Cattaneo F, Festa C, Zollo F, Iaccio A, Ammendola R, Incollingo F, Iorizzi M (2011) Imbricatolic acid from Juniperus communis L. prevents cell cycle progression in CaLu-6 cells. Planta Med 77(16):1822–1828 Dzharullaeva SSh (2009) Phytochemical investigation of Juniper rufescens leaves and fruits. Georgian Med News (168):107–111

References 361 El-Ghorab A, Shaaban HA, El-Massry KF, Shibamoto T (2008) Chemical composition of volatile extract and biological activities of volatile and less-volatile extracts of juniper berry (Juniperus drupacea L.) fruit. J Agric Food Chem 56(13):5021–5025 Ennajar M, Bouajila J, Lebrihi A, Mathieu F, Abderraba M, Raies A, Romdhane M (2009) Chemical composition and antimicrobial and antioxidant activities of essential oils and various extracts of Juniperus phoenicea L. (Cupressacees). J Food Sci 74:M364–M371 Ennajar M, Bouajila J, Lebrihi A, Mathieu F, Savagnac A, Abderraba M, Raies A, Romdhane M (2010) The influence of organ, season and drying method on chemical composition and anti- oxidant and antimicrobial activities of Juniperus phoenicea L. essential oils. J Sci Food Agric 90:462–470 Ennajar M, Afloulous S, Romdhane M, Ibrahim H, Cazaux S, Abderraba M, Raies A, Bouajila J (2011) Influence of the process, season, and origin on volatile composition and antioxidant activity of Juniperus phoenicea L. leaves essential oils. J Food Sci 76:C224–C230 Filipowicz N, Kaminski M, Kurlenda J, Asztemborska M, Ochocka JR (2003) Antibacterial and antifungal activity of juniper berry oil and its selected components. Phytother Res 17(3):227–231 Gordien AY, Gray AI, Franzblau SG, Seidel V (2009) Antimycobacterial terpenoids from Juniperus communis L. (Cuppressaceae). J Ethnopharmacol 126(3):500–505 Lawrence HA, Palombo EA (2009) Activity of essential oils against Bacillus subtilis spores. J Microbiol Biotechnol 19(12):1590–1595 Lim JP, Song YC, Kim JW, Ku CH, Eun JS, Leem KH, Kim DK (2002) Free radical scavengers from the heartwood of Juniperus chinensis. Arch Pharm Res 25(4):449–452 Marino A, Bellinghieri V, Nostro A, Miceli N, Taviano MF, Guvenc A, Bisignano G (2010) In vitro effect of branch extracts of Juniperus species from Turkey on Staphylococcus aureus biofilm. FEMS Immunol Med Microbiol 59(3):470–476 Martz F, Peltola R, Fontanay S, Duval RE, Julkunen-Tiitto R, Stark S (2009) Effect of latitude and altitude on the terpenoid and soluble phenolic composition of juniper (Juniperus communis) needles and evaluation of their antibacterial activity in the boreal zone. J Agric Food Chem 57(20):9575–9584 Miceli N, Trovato A, Dugo P, Cacciola F, Donato P, Marino A, Bellinghieri V, La Barbera TM, Guvenç A, Taviano MF (2009) Comparative analysis of flavonoid profile, antioxidant and anti- microbial activity of the berries of Juniperus communis L. var. communis and Juniperus com- munis L. var. saxatilis Pall. from Turkey. J Agric Food Chem 57:6570–6577 Miceli N, Trovato A, Marino A, Bellinghieri V, Melchini A, Dugo P, Cacciola F, Donato P, Mondello L, Guvenç A, De Pasquale R, Taviano MF (2011) Phenolic composition and biologi- cal activities of Juniperus drupacea Labill. berries from Turkey. Food Chem Toxicol 49:2600–2608 Neves A, Rosa S, Gonçalves J, Rufino A, Judas F, Salgueiro L, Lopes MC, Cavaleiro C, Mendes AF (2010) Screening of five essential oils for identification of potential inhibitors of IL-1- induced Nf-kappaB activation and NO production in human chondrocytes: characterization of the inhibitory activity of alpha-pinene. Planta Med 76:303–308 Orav A, Kailas T, Muurisepp M (2010) Chemical investigation of the essential oil from berries and needles of common juniper (Juniperus communis L.) growing wild in Estonia. Nat Prod Res 24(19):1789–1799 Orhan N, Orhan IE, Ergun F (2011) Insights into cholinesterase inhibitory and antioxidant activi- ties of five Juniperus species. Food Chem Toxicol 49(9):2305–2312 Ozturk M, Tumen I, Ugur A, Aydogmus-Ozturk F, Topcu G (2011) Evaluation of fruit extracts of six Turkish Juniperus species for their antioxidant, anticholinesterase and antimicrobial activi- ties. J Sci Food Agric 91(5):867–876 Pepeljnjak S, Kosalec I, Kalodera Z, Blazevic N (2005) Antimicrobial activity of juniper berry essential oil (Juniperus communis L., Cupressaceae). Acta Pharm 55(4):417–422 Samoylenko V, Dunbar DC, Gafur MA, Khan SI, Ross SA, Mossa JS, El-Feraly FS, Tekwani BL, Bosselaers J, Muhammad I (2008) Antiparasitic, nematicidal and antifouling constituents from Juniperus berries. Phytother Res 22(12):1570–1576

362 32 Juniper Schepetkin IA, Faulkner CL, Nelson-Overton LK, Wiley JA, Quinn MT (2005) Macrophage immunomodulatory activity of polysaccharides isolated from Juniperus scopolorum. Int Immunopharmacol 5(13–14):1783–1799 Taviano MF, Marino A, Trovato A, Bellinghieri V, La Barbera TM, Guvenc A, Hurkul MM, Pasquale RD, Miceli N (2011) Antioxidant and antimicrobial activities of branches extracts of five Juniperus species from Turkey. Pharm Biol 49:1014–1022 Wanner J, Schmidt E, Bail S, Jirovetz L, Buchbauer G, Gochev V, Girova T, Atanasova T, Stoyanova A (2010) Chemical composition and antibacterial activity of selected essential oils and some of their main compounds. Nat Prod Commun 5(9):1359–1364 Wei A, Shibamoto T (2007) Antioxidant activities and volatile constituents of various essential oils. J Agric Food Chem 55(5):1737–1742

Chapter 33 Lavender Botanical Name: Lavandula angustifolia Mill. Synonyms: Lavandula officinalis Chaix.; Lavandula spica L.; Lavandula vera DC.; common lavender; English lavender from France is Family: often traded as French Lavender. Common Names: Lamiaceae (Labiatae). French: Lavande; German: Lavendel; Spanish: Lavanda; Italian: Lavanda. Introduction History Lavender (Lavandula officinalis) is native to the Mediterranean region and is cultivated in France, Spain, and elsewhere. It was used for aromatic purposes by the Romans in baths. It is effective to cure headaches, especially when related to stress, and clear depression associated with weakness and depression. Externally, lavender oil has been used as a stimulating liniment to help ease aches and pains of rheuma- tism. Lavender has several properties: carminative, relieves muscle spasms, antide- pressant, antiseptic, antibacterial, and stimulates blood flow. Lavender is an aromatic flower used to make a delicious tea that calms the nerves. One teaspoon per pot of tea is the normal potency. Lavender oil is the most popular and most versatile essen- tial oil associated with aromatherapy and traditional uses. The Latin name Lavandula is derived from the Latin word lavare, meaning “to wash,” which comes from the ancient use of this plant to perfume water for bathing. The name angustifolia means narrow-leaved. Lavandula was known to the earliest botanical writers and the first written account is by Greek scholar Theophrastus (370–285 BC). Pure lavender has been highly regarded for the skin. The French scientist Rene Gattefosse was the first to discover these properties when he severely burned his arm in a laboratory accident. Lavender may also be used to cleanse cuts, bruises, and skin irritations. Its aromatic D.J. Charles, Antioxidant Properties of Spices, Herbs and Other Sources, 363 DOI 10.1007/978-1-4614-4310-0_33, © Springer Science+Business Media New York 2013

364 33 Lavender influences are health, love, peace, and higher consciousness. The oil can be diffused or applied topically. It is safe for use on small children; it may be added to food or water as a dietary supplement. Producing Regions Indigenous to the western Mediterranean region. Now cultivated all over the world. France, Spain, Australia, Bulgaria, Ukraine, England, Russia, Italy, and China are the major producers. Botanical Description It is an aromatic evergreen, perennial woody shrub, reaching up to 1-m (3 ft) height. It has pale green or silvery, narrow, linear leaves, with beautiful violet-blue or pur- ple-blue flowers on attractive blunt spikes. The plant is highly aromatic. There are several species of Lavandula, plus a number of taxa and hybrids. The important species of lavender are Lavandula × intermedia (Lavandin), Lavandula latifolia (Spike lavender), and Lavandula stoechas (Spanish lavender). Parts Used Freshly cut and partially dried leaves, essential oil. Flavor and Aroma Lavender has a very floral, fruity, and herbaceous aroma. It has a sweet, floral- herbaceous, refreshing, pleasant balsamic-woody undertone. Active Constituents Essential oil (1–3%) containing more than 100 constituents including linalyl ace- tate, linalool, cis- and trans-b-ocimene, terpinen-4-ol, lavandulol, lavandulyl ace- tate, 1,8-cineole, limonene, etc.; flavonoids, triterpenoids, tannins (5–10%), and coumarins.

Medicinal Uses and Functional Properties 365 Preparation and Consumption Lavender flowers and leaves are used in flavored vinegars, jellies, and sparingly in salads. Flowers and oils are used as flavorings in tea formulations. Lavender oil and absolute are used as natural food flavors. They are used in baked goods, soft candy, gelatin, frozen dairy, pudding, and alcoholic and nonalcoholic beverages (Fenaroli 1997). Lavender oils are used in colognes, fougeres, chypres, abres, and other floral perfumes and soaps. Medicinal Uses and Functional Properties Lavender is stated to be carminative, spasmolytic, and antidepressant. Lavender has antioxidant, antimicrobial, antibacterial, larvicidal, pharmacological, and other functions (Hohmann et al. 1999; Lis-Balchin et al. 1998; Lis-Balchin 1997, 2002; Lee and Shibamoto 2002; Broudiscou and Lassalas 2000; Hajhashemi et al. 2003; Nitzsche et al. 2004; Kovacheva et al. 2006; Ferreira et al. 2006; Marulanda et al. 2007; Tahraoui et al. 2007; Chohan et al. 2008; Field et al. 2008; Georgiev et al. 2009; Lodhia et al. 2009; Ozcan et al. 2009; Thring et al. 2009; Arzi et al. 2010; Blazekovic et al. 2010; Conti et al. 2010; Kasper et al. 2010; Pirali-Kheirabadi and Teixeira da Silva 2010; Sokovic et al. 2010; Yang et al. 2010; Zu et al. 2010; Barker and Altman 2011; Benabdelkader et al. 2011; Komes et al. 2011; Kunicka- Styczynska et al. 2011; Sienkiewicz et al. 2011; Spiridon et al. 2011; Vakilian et al. 2011; Woronuk et al. 2011; Alnamer et al. 2012; Amira et al. 2012). Linalool, a major constituent of lavender, was reported to relax the small intestine of mouse (Imaseki and Kitabatake 1962). The essential oil of lavender had a spasmolytic action on rabbit and guinea pig gut (Shipochliev 1968). Methanolic extracts of lav- ender dried flowers, fresh flowers, and fresh leaves had a spasmolytic action on the guinea pig ileum (Hart and Lis-Balchin 2002). Buchbauer et al. (1991, 1993) showed evidence for the sedative properties of lavender essential oil as it decreased the motility of test mice and stressed animals. Linalool inhaled for 1 h was found to induce sedation in mice without significant impairment in motor abilities (Linck et al. 2009). Lewith et al. (2005) found lavender to improve insomnia. Orally admin- istered lavender capsules were found to have anxiolytic effects in humans under conditions of low anxiety (Bradley et al. 2009). Lavender oil promoted normaliza- tion of the level of total lipids and the ratio of total cholesterol to its a-fraction (Siurin 1997). The essential oil of L. stoechas showed good antimicrobial activities against different strains of bacteria, filamentous fungi, and yeasts (Benabdelkader et al. 2011). The aqueous lavender extract was shown to effectively reverse spatial learning deficits in rats with Alzheimer’s disease (Kashani et al. 2011). A recent study found that lavender oil essence can be effective in reducing perineal discom- fort following episiotomy (Sheikhan et al. 2012).

366 33 Lavender Antioxidant Properties Phenolic components in the methanolic extracts of lavender were found effective in both enzyme-dependent and enzyme-independent lipid peroxidation systems (Hohmann et al. 1999). Lavender oil is found to relieve the pain associated with rheu- matic and musculo-skeletal disorders (Billany et al. 1995). Smelling lavender essen- tial oil was shown to enhance the free radical scavenging activity and decrease the stress hormone, cortisol, which protects the body from oxidative stress (Atsumi and Tonosaki 2007). Rosmarinic acid found in lavender has been shown to have antibacte- rial, antiviral, anti-inflammatory, and antioxidant activities (Petersen and Simmonds 2003). Kovacheva et al. (2006) evaluated the radical scavenging capacities of extracts and preparations from lavender plant cell culture with different rosmarinic acid con- tent and compared them with pure rosmarinic and caffeic acids. Their results showed that extracts and preparations from lavender possessed strong radical scavengers. Nitzsche et al. (2004) showed that both rosmarinic acid and caffeic acid from lavender cell cultures had antioxidative activity. The antioxidant activity of Lavandula species (L. × intermedia and L. angustifolia) was found to be mainly due to the presence of rosmarinic acid. And there was a strong correlation between the antioxidant activity and polyphenol contents of the extracts (Blazekovic et al. 2010). Lavender essential oil was found to have strong DPPH radical scavenging activity (Yang et al. 2010). Spiridon et al. (2011) reported the antioxidant activities of oregano, lavender, and lemon balm. The phenolic acids identified in the analyzed species were ferulic, rosmarinic, p-coumaric, and caffeic, while predominant flavonoids were quercetin, apigenin, and kaempferol, which were present as glucosides. Regulatory Status GRAS 182.10 and GRAS 182.20. Standard ISO 3515 (Oil). References Alnamer R, Alaoui K, Bouidida el H, Benjouad A, Cherrah Y (2012) Sedative and hypnotic activi- ties of the methanolic and aqueous extracts of Lavandula officinalis from Morocco. Adv Pharmacol Sci 2012:270824 Amira S, Dade M, Schinella G, Riíos JL (2012) Anti-inflammatory, anti-oxidant, and apoptotic activities of four plant species used in folk medicine in the Mediterranean basin. Pak J Pharm Sci 25(1):65–72

References 367 Arzi A, Sela L, Green A, Givaty G, Dagan Y, Sobel N (2010) The influence of odorants on respiratory patterns in sleep. Chem Senses 35:31–40 Atsumi T, Tonosaki K (2007) Smelling lavender and rosemary increases free radical scavenging activity and decreases cortisol level in saliva. Psychiatry Res 150:89–96 Barker SC, Altman PM (2011) An ex vivo, assessor blind, randomised, parallel group, comparative efficacy trial of the ovicidal activity of three pediculicides after a single application – mela- leuca oil and lavender oil, eucalyptus oil and lemon tea tree oil, and a “suffocation” pediculi- cide. BMC Dermatol 11:14 Benabdelkader T, Zitouni A, Guitton Y, Jullien F, Maitre D, Casabianca H, Legendre L, Kameli A (2011) Essential oils from wild populations of Algerian Lavandula stoechas L.: composition, chemical variability, and in vitro biological properties. Chem Biodivers 8:937–953 Billany MR, Denman S, Jameel S, Sugden JK (1995) Topical antirheumatic agents as hydroxyl radical scavengers. Int J Pharm 124:279–283 Blazekovic B, Vladimir-Knezevic S, Brantner A, Stefan MB (2010) Evaluation of antioxidant potential of Lavandula × intermedia Emeric ex Loisel. ‘Budrovka’: a comparative study with L. angustifolia Mill. Molecules 15:5971–5987 Bradley BF, Brown SL, Chu S, Lea RW (2009) Effects of orally administered lavender essential oil on responses to anxiety-provoking film clips. Hum Psychopharmacol 24(4):319–330 Broudiscou LP, Lassalas B (2000) Effects of Lavandula officinalis and Equisetum arvense dry extracts and isoquercitrin on the fermentation of diets varying in forage contents by rumen microorganisms in batch culture. Reprod Nutr Dev 40(5):431–440 Buchbauer G, Jirovetz L, Jager W, Dietrich H, Plank C (1991) Aromatherapy: evidence for seda- tive effects of the essential oil of lavender after inhalation. Z Naturforsch 46:1067–1072 Buchbauer G, Jager W, Jirovetz L, Ilmberger J, Dietrich H (1993) Therapeutic properties of essen- tial oils and fragrances. In: Teramishu R, Buttery RG, Sugisawa H (eds) Bioactive volatile compounds from plants, ACS symposium series 525, American Chemical Society, Washington DC, pp 159–165 Chohan M, Forster-Wilkins G, Opara EI (2008) Determination of the antioxidant capacity of culi- nary herbs subjected to various cooking and storage processes using the ABTS(*+) radical cation assay. Plant Foods Hum Nutr 63:47–52 Conti B, Canale A, Bertoli A, Gozzini F, Pistelli L (2010) Essential oil composition and larvicidal activity of six Mediterranean aromatic plants against the mosquito Aedes albopictus (Diptera: Culicidae). Parasitol Res 107(6):1455–1461 Fenaroli G (1998) Fenaroli’s Handbook of Flavor Ingredients. Vol 1, 3rd ed. CRC Press, Boca Raton Ferreira A, Proença C, Serralheiro ML, Araújo ME (2006) The in vitro screening for acetylcholin- esterase inhibition and antioxidant activity of medicinal plants from Portugal. J Ethnopharmacol 108(1):31–37 Field T, Field T, Cullen C, Largie S, Diego M, Schanberg S, Kuhn C (2008) Lavender bath oil reduces stress and crying and enhances sleep in very young infants. Early Hum Dev 84(6): 399–401 Georgiev M, Abrashev R, Krumova E, Demirevska K, Ilieva M, Angelova M (2009) Rosmarinic acid and antioxidant enzyme activities in Lavandula vera MM cell suspension culture: a com- parative study. Appl Biochem Biotechnol 159:415–425 Hajhashemi V, Ghannadi A, Sharif B (2003) Anti-inflammatory and analgesic properties of the leaf extracts and essential oil of Lavandula angustifolia Mill. J Ethnopharmacol 89(1):67–71 Hart S, Lis-Balchin M (2002) Pharmacology of Lavandula essential oils and extracts in vitro and in vivo. In: Lis-Balchin M (ed) Lavender; the genus Lavandula, Medicinal and aromatic plants – industrial profiles. Taylor and Francis, London, pp 140–154 Hohmann J, Zupko I, Redei D, Csanyi M, Falkay G, Mathe I, Janicsak G (1999) Protective effects of the aerial parts of Salvia officinalis, Melissa Officinalis and Lavandula angustifolia and their constituents against enzyme-dependent and enzyme-independent lipid peroxidation. Planta Med 65(6):576–578

368 33 Lavender Imaseki I, Kitabatake Y (1962) Studies on effect of essential oils and their components on the isolated intestines of mice. Yakugaku Zasshi 82:1326–1328 Kashani MS, Tavirani MR, Talaei SA, Salami M (2011) Aqueous extract of lavender (Lavandula angustifolia) improves the spatial performance of a rat model of Alzheimer’s disease. Neurosci Bull 27(2):99–106 Kasper S, Gastpar M, Muller WE, Volz HP, Moller HJ, Dienel A, Schlafke S (2010) Efficacy and safety of silexan, a new, orally administered lavender oil preparation, in subthreshold anxiety disorder – evidence from clinical trials. Wien Med Wochenschr 160(21–22):547–556 Komes D, Belščak-Cvitanović A, Horžić D, Rusak G, Likić S, Berendika M (2011) Phenolic com- position and antioxidant properties of some traditionally used medicinal plants affected by the extraction time and hydrolysis. Phytochem Anal 22:172–180 Kovacheva E, Georgiev M, Pashova S, Angelova M, Ilieva M (2006) Radical quenching by ros- marinic acid from Lavandula vera MM cell culture. Z Naturforsch C 61(7–8):517–520 Kunicka-Styczynska A, Sikora M, Kalemba D (2011) Lavender, tea tree and lemon oils as antimi- crobials in washing liquids and soft body balms. Int J Cosmet Sci 33(1):53–61 Lee KG, Shibamoto T (2002) Determination of antioxidant potential of volatile extracts isolated from various herbs and spices. J Agric Food Chem 50(17):4947–4952 Lewith GT, Godfrey AD, Prescott P (2005) A single-blinded, randomized pilot study evaluating the aroma of Lavandula angustifolia as a treatment for mild insomnia. J Altern Complement Med 11(4):631–637 Linck VM, da Silva AL, Figueiro M, Piato AL, Herrmann AP, Dupont Birck F, Caramao EB, Nunes DS, Moreno PR, Elisabetsky E (2009) Inhaled linalool-induced sedation in mice. Phytomedicine 16(4):303–307 Lis-Balchin M (1997) Essential oils and ‘aromatherapy’: their modern role in healing. J R Soc Health 117(5):324–329 Lis-Balchin M (ed) (2002) Lavender; the genus Lavandula, Medicinal and aromatic plants – industrial profiles. Taylor and Francis, London Lis-Balchin M, Deans SG, Eaglesham E (1998) Relationship between bioactivity and chemical composition of commercial essential oils. Flavor Fragr J 13:98–104 Lodhia MH, Bhatt KR, Thaker VS (2009) Antibacterial activity of essential oils from palmarosa, evening primrose, lavender and tuberose. Indian J Pharm Sci 71(2):134–136 Marulanda A, Porcel R, Barea JM, Azcón R (2007) Drought tolerance and antioxidant activities in lavender plants colonized by native drought-tolerant or drought-sensitive Glomus Species. Microb Ecol 54:543–552 Nitzsche A, Tokalov SV, Gutzeit HO, Ludwig-Müller J (2004) Chemical and biological character- ization of cinnamic acid derivatives from cell cultures of lavender (Lavandula officinalis) induced by stress and jasmonic acid. J Agric Food Chem 52(10):2915–2923 Ozcan MM, Erel O, Herken EE (2009) Antioxidant activity, phenolic content, and peroxide value of essential oil and extracts of some medicinal and aromatic plants used as condiments and herbal teas in Turkey. J Med Food 12(1):198–202 Petersen M, Simmonds MS (2003) Rosmarinic acid. Phytochemistry 62(2):121–125 Pirali-Kheirabadi K, Teixeira da Silva JA (2010) Lavandula angustifolia essential oil as a novel and promising natural candidate for tick (Rhipicephalus (Boophilus) annulatus) control. Exp Parasitol 126(2):184–186 Sheikhan F, Jahdi F, Khoei EM, Shamsalizadeh N, Sheikhan M, Haghani H (2012) Episiotomy pain relief: use of Lavender oil essence in primiparous Iranian women. Complement Ther Clin Pract 18(1):66–70 Shipochliev T (1968) Pharmacological investigation into several essential oils. First communica- tion. Effect on the smooth musculature. Vet Med Nauki 5:63–69 Sienkiewicz M, Kalemba D, Wasiela M (2011) Sensitivity assessment of thyme and lavender essential oils against clinical strains of Escherichia coli for their resistance. Med Dosw Mikrobiol 63(3):273–281

References 369 Siurin SA (1997) Effects of essential on lipid peroxidation and lipid metabolism in patients with chronic bronchitis. Klin Med Moskau 75:43–45 Sokovic M, Glamoclija J, Marin PD, Brkic D, van Griensven LJ (2010) Antibacterial effects of the essential oils of commonly consumed medicinal herbs using an in vitro model. Molecules 15(11):7532–7546 Spiridon I, Colceru S, Anghel N, Teaca CA, Bodirlau R, Armatu A (2011) Antioxidant capacity and total phenolic contents of oregano (Origanum vulgare), lavender (Lavandula angustifolia) and lemon balm (Melissa officinalis) from Romania. Nat Prod Res 25(17):1657–1661 Tahraoui A, El-Hilaly J, Israili ZH, Lyoussi B (2007) Ethnopharmacological survey of plants used in the traditional treatment of hypertension and diabetes in south-eastern Morocco (Errachidia province). J Ethnopharmacol 110(1):105–117 Thring TS, Hili P, Naughton DP (2009) Anti-collagenase, anti-elastase and anti-oxidant activities of extracts from 21 plants. BMC Complement Altern Med 9:27 Vakilian K, Atarha M, Bekhradi R, Chaman R (2011) Healing advantages of lavender essential oil during episiotomy recovery: a clinical trial. Complement Ther Clin Pract 17(1):50–53 Woronuk G, Demissie Z, Rheault M, Mahmoud S (2011) Biosynthesis and therapeutic properties of Lavandula essential oil constituents. Planta Med 77(1):7–15 Yang SA, Jeon SK, Lee EJ, Shim CH, Lee IS (2010) Comparative study of the chemical composi- tion and antioxidant activity of six essential oils and their components. Nat Prod Res 24(2):140–151 Zu Y, Yu H, Liang L, Fu Y, Efferth T, Liu X, Wu N (2010) Activities of ten essential oils towards Propionibacterium acnes and PC-3, A-549 and MCF-7 cancer cells. Molecules 15(5): 3200–3210

Chapter 34 Lemon Balm Botanical Name: Melissa officinalis L. Italian: Synonyms: bee balm, balm, Melissa, Melissa balm. Family: Lamiaceae (Labiatae). Common Names: French: citronelle; German: zitronenmelisse; melissa; Spanish: balsamita maior. Introduction History Lemon balm, called bosem in the Hebrew, means fragrance, and probably originated in the Middle East. It has been cultivated in the Mediterranean region for about 2,000 years. The Latin name melissa was coined in the Middle Ages from Greek melisso- phyllon, meaning “bee-leaf,” because the plant is rich in nectar and commonly planted to feed bees; that name is akin to Latin mel “honey” and also the British term for orange rind jelly, marmalade. It is a popular spice in Mediterranean cooking, though it is more important as a medicinal herb than as a seasoning. The London Dispensary (1696) says, “An essence of Balm, given in Canary wine, every morning will renew youth, strengthen the brain, relieve languishing nature and prevent bald- ness.” John Evelyn wrote, “Balm is sovereign for the brain, strengthening the mem- ory and powerfully chasing away melancholy.” Balm steeped in wine we are told again, “comforts the heart and driveth away melancholy and sadness.” Gerard says, “It is profitably planted where bees are kept. The hives of bees being rubbed with the leaves of bawme, causeth the bees to keep together, and causeth others to come with them.” The great Pliny said, “When they are strayed away, they do find their way home by it.” He also said, “It is of so great virtue that though it be but tied to his sword that hath given the wound it stauncheth the blood”. Gerard also said, “The juice of Balm glueth together greene wounds,” and gives the opinion of Pliny and Dioscorides that “Balm, being leaves steeped in wine, and the wine drunk, and the D.J. Charles, Antioxidant Properties of Spices, Herbs and Other Sources, 371 DOI 10.1007/978-1-4614-4310-0_34, © Springer Science+Business Media New York 2013

372 34 Lemon Balm leaves applied externally, were considered to be a certain cure for the bites of venomous beasts and the stings of scorpions.” The Muslim herbalist Avicenna recommended lemon balm “to make the heart merry.” Paracelsus claimed this herb could com- pletely revitalize the body. The seventeenth century herbalist Culpeper says the herb “be kept in every gentlewomans house…. It causeth the Mind and Heart to become merry… and driveth away troublesome cares.” The fourteenth century French King Charles V drank its tea every day to keep his health, as did the Prince of Glamorgan, who lived to be 108 years old. The seventeenth century Carmelite nuns made the famous Carmelite water, which combined lemon balm with lemon-peel, nutmeg, coriander, and angelica root. It was sold for centuries as Eau de Melisse de Carmes. The true Carmelite water is still sold in Germany as Klosterfqu Melissengeist. Producing Regions Lemon balm is native to the east Mediterranean region and west Asia. It is now cultivated in Middle East, North Africa, Egypt, Italy, Hungary, and the USA. Botanical Description It is a small plant up to 1 m (2 ft) high, with square stems. It has very aromatic, toothed leaves which emit a fragrant lemon odor when bruised. The flowers, white or yellowish, are in loose, small bunches from the axils of the leaves and bloom from June to October. The flowers consist of five fused sepals, five petals, two or four stamens, and four lobed ovaries. The seeds are very small, ovate, dark brown, or black in color. The plant dies down in winter, but the root is perennial. Parts Used Leaves (fresh or dried, whole or chopped). Flavor and Aroma Lemon balm has a sweet, lemon, fresh aroma. Fresh, lemony, sweet taste, with a slightly mint hint. The oil has a very pleasant fresh sweet lemony aroma. Active Constituents It has essential oil (0.1% average, with citral-geranial and neral, linalool, eugenol, cit- ronellal, geraniol), tannins, bitter principle, resin, polyphenols, flavonoids, succinic acid,

Medicinal Uses and Functional Properties 373 and rosmarinic acid (Carnat et al. 1998; Saglam et al. 2004; Sari and Ceylan 2002; Capecka et al. 2005; Ivanova et al. 2005; Sanchez-Medina et al. 2007; Awad et al. 2009). The fresh herb has phenolics, l-ascorbic acid, and carotenoids. Polyphenolic compounds (rosmarinic acid, caffeic acid, and protocatechuic acid), essential oils (citral), monoterpenoid aldehydes, sesquiterpenes, flavonoids (luteolin), and tannins have been reported in lemon balm (Carnat et al. 1998; Guginski et al. 2009). Preparation and Consumption Lemon balm goes well with teas, vinegars, stewed fruits, jellies, puddings, and cus- tards (Bozan 1995; Zeybek 1995). It can be added to fish, poultry, eggs, salads, and soups. It is also used as a garnish or added to salads for a lemony flavor. It is a com- mon flavoring in fruit drinks, iced teas, and fruit-based desserts. It can be made into a sauce with virgin olive oil, garlic, ginger, fruits, and almonds. Medicinal Uses and Functional Properties Traditionally it has been used to heal wounds, sores, and bee and wasp stings, to relieve tension, calming nerves, and for headaches (Horrigan 2005). It was used as a drink to ensure longevity and aptly called “elixir of life” in Europe. It is used to treat asthma, stomach ailments, indigestion, menstrual cramps, and fevers (Herodez et al. 2003). It reduces sores from genital or oral herpes (Allahverdiyev et al. 2004). Aqueous and alcoholic extracts from the aerial part of Melissa officinalis are tradi- tionally used in the treatment of fevers and colds, indigestion associated with ner- vous tension, hyperthyroidism, depression, mild insomnia, epilepsy, headaches, toothaches, and other ailments (Carnat et al. 1998; Herodez et al. 2003; Salah and Jager 2005; Dastmalchi et al. 2008; Howes and Perry 2011). Lemon balm has been shown to have antibacterial, antimicrobial, antimutagenic, antiviral, antifungal, anti- tumor, and antioxidant properties (Mimica-Dukic et al. 2004; Blomhoff 2004; Hamer et al. 2005; Uzun et al. 2004; Dragland et al. 2003; Bolkent et al. 2005; Kennedy and Scholey 2006; Apak et al. 2006; Mazzanti et al. 2008; Awad et al. 2009; Chung et al. 2010; de Ciriano et al. 2010; Lahucky et al. 2010; Komes et al. 2011; Lara et al. 2011; Obulesu and Rao 2011; Petrovic et al. 2011; Spiridon et al. 2011). Rosmarinic acid in lemon balm appears to contribute for the antinociceptive property of the ethanolic extract (Guginski et al. 2009). Lemon balm was found to be the most effective plant against five food spoilage yeasts (Araujo et al. 2003). The essential oil of lemon balm inhibited all the yeast species and the fungitoxic effect was attributed to citral, the major constituent. It also inhibited some antibiotic resistant bacteria (Nascimento et al. 2000). The major compounds found to be the most powerful scavenging compounds in lemon balm were neral, geranial, citro- nellal, menthone, isomenthone, and b-caryophyllene (Mimica-Dukic et al. 2004). Lemon balm treatment is suggested for treating active Herpes simplex lesions or

374 34 Lemon Balm preventing recurrences (Gaby 2006). Lemon balm essential oil was shown to be an efficient hypoglycemic agent, and this was probably due to the enhanced glucose uptake and metabolism in the liver and adipose tissue, and the inhibition of gluco- neogenesis in the liver (Chung et al. 2010). Ethanol extract of lemon balm exerted an antigenotoxic effect on the blood cells of mice treated with the alkylating agent (MMS) in all doses (de Carvalho et al. 2011). Antioxidant Properties Ethanol extract of lemon balm was found to improve the oxidation stability of sunflower oil (Marinova and Yanishlieva 1997). Lemon balm possesses strong anti- oxidant activity due to its phenolic constituents rosmarinic acid and caffeic acid (Triantaphyllou et al. 2001; Labuda et al. 2002). Dragland et al. (2003) reported lemon balm to contain very high concentrations of antioxidants (>75 mmol/100 g) and suggested plant oxidants to be a better source of dietary antioxidants than many other food groups like fruits, berries, cereals, and vegetables. Lemon balm extract was found to decrease serum cholesterol and lipid levels in the hyperlipidemic ani- mals (Bolkent et al. 2005). Essential oil of lemon balm was found to possess anti- oxidant activity and very effective against a series of human cancer cell lines (de Sousa et al. 2004). Lemon balm at a concentration of 1.5% w/w increased by 150% the antioxidant capacity of a salad portion (Ninfali et al. 2005). In the xanthine oxi- dase system, the extracts of lemon balm showed very efficient antioxidant result (Schempp et al. 2006). An aqueous extract of lemon balm had significant antioxi- dant capacity—0.99 mmol trolox equivalent (Apak et al. 2006). Ivanova et al. (2005) reported lemon balm extract to have 1,370.09 mM total phenols and an anti- oxidant capacity of 4.06 TEAC. Rosmarinic acid, a great antioxidant, was found in higher concentrations in tinctures made with dried plant material (Sanchez-Medina et al. 2007). The methanol extract of lemon balm was a potent in vitro inhibitor of rat brain GABA transaminase, an enzyme target in the therapy of anxiety, epilepsy, and related neurological disorders (Awad et al. 2009). The lyophilized extract of lemon balm showed strong antioxidant activity and high total phenolic content (de Ciriano et al. 2010). Lemon balm essential oil was found to have strong antioxidant activity (Chung et al. 2010). Extraction time was important in extracting the poly- phenolic compounds and it also affected their antioxidant activities (Komes et al. 2011). Origanum vulgare and Melissa officinalis extracts were found to exhibit the most effective antioxidant capacity in scavenging DPPH radicals, while Lavandula angustifolia was less active (Spiridon et al. 2011). Regulatory Status GRAS 182.10 and GRAS 182.20.

References 375 References Allahverdiyev A, Duran N, Ozguven M, Koltas S (2004) Antiviral activity of the volatile oils of Melissa officinalis L. against Herpes simplex virus type-2. Phytomedicine 11(7-8):657–661 Apak R, Guclu K, Ozyurek M, Esin Karademir S, Ercag E (2006) The cupric ion reducing antioxi- dant capacity and polyphenolic content of some herbal teas. Int J Food Sci Nutr 57(5–6): 292–304 Araujo C, Sousa MJ, Ferreira MF, Leao C (2003) Activity of essential oils from Mediterranean Lamiaceae species against food spoilage yeasts. J Food Prot 66(4):625–632 Awad R, Muhammad A, Durst T, Trudeau VL, Arnason JT (2009) Bioassay-guided fractionation of lemon balm (Melissa officinalis L.) using an in vitro measure of GABA transaminase activ- ity. Phytother Res 23(8):1075–1081 Blomhoff R (2004) Antioxidants and oxidative stress. Tidsskr Nor Laegeforen 124(12): 1643–1645 Bolkent S, Yanardag R, Karabulut-Bulan O, Yesilyaprak B (2005) Protective role of Melissa officinalis L. extract on liver of hyperlipidemic rats: a morphological and biochemical study. J Ethnopharmacol 99(3):391–398 Bozan B (1995) ESOP and therapy with plants in Europe. Anadolu University, Research Center of Medicinal and Aromatic Plants, Medicine, TAB Bulletin 11 Capecka E, Mareczek A, Leja M (2005) Antioxidant activity of fresh and dry herbs of some Lamiaceae species. Food Chemistry 93:223–226 Carnat AP, Carnat A, Fraisse D, Lamaison JL (1998) The aromatic and polyphenolic composition of lemon balm (Melissa officinalis L. subsp. officinalis) tea. Pharm Acta Helv 72:301–305 Chung MJ, Cho SY, Bhuiyan MJ, Kim KH, Lee SJ (2010) Anti-diabetic effects of lemon balm ( Melissa officinalis) essential oil on glucose- and lipid-regulating enzymes in type 2 diabetic mice. Br J Nutr 104:180–188 Dastmalchi K, Dorman HJD, Oinonen PP, Darwis Y, Laakso I, Hiltunen R (2008) Chemical com- position and in vitro antioxidative activity of a lemon balm (Melissa officinalis L.) extract. LWT Food Sci Technol 41:391–400 de Carvalho NC, Correa-Angeloni MJ, Leffa DD, Moreira J, Nicolau V, de Aguiar AP, Rossatto AE, de Andrade VM (2011) Evaluation of the genotoxic and antigenotoxic potential of Melissa officinalis in mice. Genet Mol Biol 34(2):290–297 de Ciriano MG, Rehecho S, Calvo MI, Cavero RY, Navarro I, Astiasaran I, Ansorena D (2010) Effect of lyophilized water extracts of Melissa officinalis on the stability of algae and linseed oil-in- water emulsion to be used as a functional ingredient in meat products. Meat Sci 85:373–377 de Sousa AC, Alviano DS, Blank AF, Alves PB, Alviano CS, Gattass CR (2004) Melissa officinalis L. essential oil: antitumoral and antioxidant activities. J Pharm Pharmacol 56(5):677–681 Dragland S, Senoo H, Wake K, Holte K, Blomhoff R (2003) Several culinary and medicinal herbs are important sources of dietary antioxidants. J Nutr 133(5):1286–1290 Gaby AR (2006) Natural remedies for Herpes simplex. Altern Med Rev 11(2):93–101 Guginski G, Luiz AP, Silva MD, Massaro M, Martins DF, Chaves J, Mattos RW, Silveira D, Ferreira VM, Calixto JB, Santos AR (2009) Mechanisms involved in the antinociception caused by ethanolic extract obtained from the leaves of Melissa officinalis (lemon balm) in mice. Pharmacol Biochem Behav 93:10–16 Hamer M, Owen G, Kloek J (2005) The role of functional foods in the psychobiology of health and disease. Nutr Res Rev 18(1):77–88 Herodez SS, Hadolin M, Skerget M, Knez Z (2003) Solvent extraction study of antioxidants from Balm (Melissa officinalis L.) leaves. Food Chem 80:275–282 Horrigan C (2005) Aromatherapy in the management and treatment of rheumatoid and musculo- skeletal autoimmune disorders: Part III. The International Journal of Aromatherapy 15:15–23 Howes MJ, Perry E (2011) The role of phytochemicals in the treatment and prevention of dementia. Drugs Aging 28(6):439–468 Ivanova D, Gerova D, Chervenkov T, Yankova T (2005) Polyphenols and antioxidant capacity of Bulgarian medicinal plants. J Ethnopharmacol 96(1–2):145–150

376 34 Lemon Balm Kennedy DO, Scholey AB (2006) The psychopharmacology of European herbs with cognition- enhancing properties. Curr Pharm Des 12(35):4613–4623 Komes D, Belscak-Cvitanovic A, Horzic D, Rusak G, Likic S, Berendika M (2011) Phenolic com- position and antioxidant properties of some traditionally used medicinal plants affected by the extraction time and hydrolysis. Phytochem Anal 22:172–180 Labuda J, Buckova M, Heilerova L, Caniova-Ziakova A, Brandsteterova E, Mattusch J, Wennrich R (2002) Detection of antioxidative activity of plant extracts at the DNA-modified screen- printed electrode. Sensor 2(1):1–10 Lahucky R, Nuernberg K, Kovac L, Bucko O, Nuernberg G (2010) Assessment of the antioxidant potential of selected plant extracts – in vitro and in vivo experiments on pork. Meat Sci 85(4):779–784 Lara MS, Gutierrez JI, Timon M, Andres AI (2011) Evaluation of two natural extracts (Rosmarinus officinalis L. and Melissa officinalis L.) as antioxidants in cooked pork patties packed in MAP. Meat Sci 88:481–488 Marinova EM, Yanishlieva NV (1997) Antioxidative activity of extracts from selected species of the family Lamiaceae in sunflower oil. Food Chem 58(3):245–248 Mazzanti G, Battinelli L, Pompeo C, Serrilli AM, Rossi R, Sauzullo I, Mengoni F, Vullo V (2008) Inhibitory activity of Melissa officinalis L. extract on Herpes simplex virus type 2 replication. Nat Prod Res 22(16):1433–1440 Mimica-Dukic N, Bozin B, Sokovic M, Simin N (2004) Antimicrobial and antioxidant activities of Melissa officinalis L. (Lamiaceae) essential oil. J Agric Food Chem 52(9):2485–2489 Nascimento GGF, Locatelli J, Freitas PC, Silva GL (2000) Antibacterial activity of plant extracts and phytochemicals on antibiotic-resistant bacteria. Braz J Microbiol 31:247–256 Ninfali P, Mea G, Giorgini S, Rocchi M, Bacchiocca M (2005) Antioxidant capacity of vegetables, spices and dressings relevant to nutrition. Br J Nutr 93(2):257–266 Obulesu M, Rao DM (2011) Effect of plant extracts on Alzheimer’s disease: an insight into thera- peutic avenues. J Neurosci Rural Pract 2:56–61 Petrovic V, Marcincak S, Popelka P, Simkova J, Martonova M, Buleca J, Marcincakova D, Tuckova M, Molnar L, Kovac G (2011) The effect of supplementation of clove and agrimony or clove and lemon balm on growth performance, antioxidant status and selected indices of lipid profile of broiler chickens. J Anim Physiol Anim Nutr (Berl) 10.1111/j.1439-0396 Saglam C, Atakisi I, Turhan H, Arslanoglu F, Onemli F (2004) Effect of propagation method, plant density, and age on lemon balm (Melissa officinalis) herb and oil yield. New Zealand Journal of Crop and Horticultural Science 32:419–423 Salah SM, Jager AK (2005) Screening of traditionally used Lebanese herbs for neurological activi- ties. J Ethnopharmacol 97:145–149 Sanchez-Medina A, Etheridge CJ, Hawkes GE, Hylands PJ, Pendry BA, Hughes MJ, Corcoran O (2007) Comparison of rosmarinic acid content in commercial tinctures produced from fresh and dried lemon balm (Melissa officinalis). J Pharm Pharm Sci 10(4):455–463 Sari AO, Ceylan A (2002) Yield characteristics and essential oil composition of lemon balm (Melissa officinalis L.) grown in the Aegean Region of Turkey. Turkish Journal of Agriculture and Forestry 26:217–224 Schempp H, Weiser D, Kelber O, Elstner EF (2006) Radical scavenging and anti-inflammatory properties of STW 5 (Iberogast) and its components. Phytomedicine 13(Suppl 5):36–44 Spiridon I, Colceru S, Anghel N, Teaca CA, Bodirlau R, Armatu A (2011) Antioxidant capacity and total phenolic contents of oregano (Origanum vulgare), lavender (Lavandula angustifolia) and lemon balm (Melissa officinalis) from Romania. Nat Prod Res 25(17):1657–1661 Triantaphyllou K, Blekas G, Boskou D (2001) Antioxidative properties of water extracts obtained from herbs of the species Lamiaceae. Int J Food Sci Nutr 52(4):313–317 Uzun E, Sariyar G, Adsersen A, Karakoc B, Otuk G, Oktayoglu E, Pirildar S (2004) Traditional medicine in Sakarya province (Turkey) and antimicrobial activities of selected species. J Ethnopharmacol 95(2–3):287–296 Zeybek Z (1995) An overview on importance of medicinal and aromatic plants for Turkey. Workshop Proceedings of Medicinal and Aromatic Plants, May 25–26, Ege University, Agricultural Faculty, Field Crops Department and Society of Field Crops

Chapter 35 Lemongrass Botanical Names: Cymbopogon citratus (DC. ex Nees) Stapf; Cymbopogon flexuosus (Nees ex Steud.) J. F. Watson. Synonyms: Andropogon citratus DC. ex Nees; West Indian lemongrass, lemongrass, fever grass. Synonyms: Andropogon flexuosus Nees ex Steud.; East Indian lemongrass, Cochin lemongrass. Family: Poaceae. Common Names: French: herbe de citron, verveine des Indes; German: Zitronengras, Lemongras; Italian: erba di limone; Spanish: hierba de limon; Indian: bhustrina, sera; Indonesian: sere, sereh; Sinhalese: sera; Thai: takrai; Malay: serai. Introduction History The original use of lemongrass was probably as a food flavoring agent in Asia. The leaves are cooked with foods especially curries. They are perennial grasses native to tropical Asia. Fresh leaves crushed in water are used as a hair-wash and toilet water in India. Systematic cultivation and distillation of essential oil began in Kerala, India, in the 1880s. The genus name, Cymbopogon, comes from the Greek “kymbe”, meaning “boat”, and “pogon”, meaning “beard”. This reference is probably due to the shape of the grass’s tiny flowers that emerge on branched stalks. The Romans, Greeks, and Egyptians have used lemongrass for centuries as a flavoring agent in medicines and as an aromatic in cosmetics. Indonesians have used it in cooking. D.J. Charles, Antioxidant Properties of Spices, Herbs and Other Sources, 377 DOI 10.1007/978-1-4614-4310-0_35, © Springer Science+Business Media New York 2013

378 35 Lemongrass Producing Regions It is native to Asia and grows wild in tropical and subtropical regions. It is cultivated in India, the Caribbean, and Central America. East Indian lemongrass grows in eastern India, Cambodia, Singapore, and Sri Lanka. West Indian lemongrass grows in Madagascar, Guatemala, Comoro Islands, Brazil, Haiti, and Puerto Rico. Botanical Description They are tall, fast growing, herbaceous, perennial grasses up to 1.5 m (8 ft) high and very aromatic. They have sturdy stems and broad, aromatic leaves. The leaves are linear and lanceolate and the flowers are in inflorescence which are large and branched. The West Indian lemongrass is stem less with stiff tillers arising from short rhizomatous rootstock. Leaf blade is narrow, linear, and drooping with scabrous margin. Parts Used The various parts used include freshly cut and partially dried leaves, essential oil, and oleoresin. The inner stalk is used fresh, frozen, or dried. The fresh form is used whole, sliced, finely chopped, or pureed. The dried form is used ground, shredded, or whole. Flavor and Aroma It has a floral, very delicate, fresh grassy lemony aroma, lemony, with a slight hint of ginger. The essential oil has strong, lingering, fresh grassy lemon-like aroma. Active Constituents East Indian lemongrass oil—geranial up to 60%, neral up to 30%, geraniol up to 4%, limonene, linalool. West Indian lemongrass oil—geranial up to 60%, neral up to 30%, myrcene up to 20%, linalool. Lemongrass has been reported to have flavonoids and phenolic compounds, which consist of elimicin, catechol, chlorogenic acid, caffeic acid, hydroquinone, luteolin, isoorientin 2¢-O-rhamnoside, quercetin, kaempferol, and apigenin (Guanasingh and Nagarajan 1981; Matouschek and Stahl 1991; Faruq 1994; Miean and Mohamed 2001).

Antioxidant Properties 379 Preparation and Consumption Lemongrass features in Indian, Malaysian, Indonesian, and Sri Lankan dishes. It is used in major categories of food products, including meat, poultry, seafood, vegeta- ble curries, candy, desserts, and baked goods. In Thai and Sri Lankan recipes, it is used with coconut milk in chicken and seafood. In Indonesia, lemongrass is com- bined with turmeric, chili peppers, and other spices to make bumbu, a seasoning, to flavor local sauces and soups. The stems are used in pickles and flavoring mari- nades. Dried leaves are used in teas. Lemongrass oil is used in flavoring major cat- egories of food including alcoholic and nonalcoholic beverages, frozen dairy desserts, candy, gelatin, puddings, meat, and fish. Oleoresin is useful in foods, drinks, and baked goods. Medicinal Uses and Functional Properties The leaves and essential oil are used to treat dyspeptic disorders, colds, nervous conditions, and exhaustion. They have antimicrobial, sedative, spasmolytic, and carminative effects. It has also been shown to have antifungal, anti-inflammatory, antimutagenic, antimalarial, antinociceptive, larvicidal, and antibacterial effects (Viana et al. 2000; Cavalcanti et al. 2004; Tchoumbougnang et al. 2005; Wannissorn et al. 2005; Adeneye and Agbaje 2007; Lee et al. 2008; Viuda-Martos et al. 2010; Bassole et al. 2011; Cilek et al. 2011; Costa et al. 2011; Devi et al. 2011; Francisco et al. 2011; Khan and Ahmad 2011; Kumar et al. 2011; Mickiene et al. 2011; Avila- Sosa et al. 2012). Lemongrass tea, a popular Brazilian herbal medicine, was found to be toxic when administered to healthy volunteers (Leite et al. 1986). The essen- tial oil from lemongrass was reported to have a promising anticancer activity and caused loss in tumor cell viability by activating the apoptotic process (Sharma et al. 2009). Costa et al. (2011) reported the safety of lemongrass intake at the doses used in folk medicine and indicated the beneficial effect of reducing the blood cholesterol level. Antioxidant Properties Lemongrass extract and essential oil have been reported to have strong antioxidant properties (Baratta et al. 1998; Rao et al. 2009; Tiwari et al. 2010; Viuda-Martos et al. 2010; Francisco et al. 2011; Henning et al. 2011; Shah et al. 2011; Quintans- Junior et al. 2011).The hepatoprotective effect of C. citratus extract was reported to be due to its antioxidant and free radical scavenging properties (Koh et al. 2012). Lemongrass was shown to be cardioprotective and antilipid peroxidative by increasing various antioxidants at a dose of 200 mg kg−1 body weight of rats, which was comparable with that of vitamin E (Gayathri et al. 2011). The results (Tiwari et al. 2010) suggest

380 35 Lemongrass the potential use of the cytoprotective, antioxidant, and anti-inflammatory properties of C. citratus in the form of dietary component and also in formulations against lung inflammatory diseases where oxidative stress plays an important role. Lemongrass (C. citratus) was found to have NO scavenging activity and also inhibited iNOS expression (Figueirinha et al. 2010). Lemongrass extract was found to decrease cerebral lipid peroxidation (TBARS) induced by iron sulfate, sodium nitroprusside, or 3-nitropropionic acid, and showed antioxidant effect by DPPH assay (Pereira et al. 2009). Isoorientin isolated from lemongrass was shown to be an effective inhibitor of in vitro LDL oxidation and thus could be useful in preventing or attenu- ating atherosclerosis (Orrego et al. 2009). Hydroalcoholic extract of lemongrass showed significant scavenging ability of DPPH, ABTS, hydroxyl, superoxide, and nitric oxide free radicals generated in vitro and also a moderate antilipid peroxida- tive effect. It also resulted in dose-dependent decrease in the yield of radiation- induced micronuclei, and decrease in the percentage of micronuclei compared with radiation alone groups. These results indicate antigenotoxic effect which may be partly due to the antioxidant capacity (Rao et al. 2009). Citral, a major compound found in lemongrass, significantly inhibited lipopolysaccharide-induced nitric oxide production, and also effectively inhibited the transcriptional activity and expression of iNOS. It also suppressed the DNA binding activity and nuclear translocation of NF-kappa B as well as I kappa B phosphorylation (Lee et al. 2008). Caffeic acid, chlorogenic acid, neochlorogenic acid, and luteolin 6-C-fucopyranoside were found to be strong free radical scavengers in the DPPH discoloration (Tapia et al. 2007). Rabbani et al. (2006) found citral from lemongrass to significantly inhibit the for- mation of micronuclei induced by nickel. It also showed good superoxide scaveng- ing activity in citral treated groups, suggesting antioxidant action of citral to be responsible for the anti-clastogenic effect of citral against nickel chloride (Rabbani et al. 2006). Methanol extract, methanol/water extract, infusion, and decoction of lemongrass showed scavenging effect in the DPPH and superoxide anion assay and inhibited lipid peroxidation in erythrocytes, but were inactive toward xanthine oxi- dase (Cheel et al. 2005). Isoorientin and orientin isolated from lemongrass had simi- lar activities toward DPPH and lipid peroxidation, while caffeic and chlorogenic acids isolated from lemongrass were active superoxide anion scavengers, and had strong effect toward DPPH. Caffeic acid from lemongrass inhibited lipid peroxida- tion (Cheel et al. 2005). Citral from lemongrass induced glutathione S-transferase in mouse skin, implying antioxidant role of citral, and providing new insights into skin cancer prevention (Nakamura et al. 2003). Organic lemongrass extract enriched in polyphenols caused relaxation action in the mesenteric preparation compared to aortic rings, and appeared to be mediated via NO-independent and non-prostanoid mechanisms (Abeywardena et al. 2002). Regulatory Status GRAS 182.20.

References 381 Standard ISO 4718 (Oil of C. flexuosus), ISO 3217 (Oil of C. citratus). References Abeywardena M, Runnie I, Nizar M, Suhaila M, Head R, Momamed S (2002) Polyphenol-enriched extract of oil palm fronds (Elaeis guineensis) promotes vascular relaxation via endothelium- dependent mechanisms. Asia Pac J Clin Nutr 11(Suppl 7):S467–472 Adeneye AA, Agbaje EO (2007) Hypoglycemic and hypolipidemic effects of fresh leaf aqueous extract of Cymbopogon citratus Stapf in rats. J Ethnopharmacol 112:440–444 Avila-Sosa R, Palou E, Jimenez Munguia MT, Nevarez-Moorillon GV, Navarro Cruz AR, Lopez- Malo A (2012) Antifungal activity by vapor contact of essential oils added to amaranth, chito- san, or starch edible films. Int J Food Microbiol 153(1–2):66–72 Baratta MT, Dorman HJD, Deans SG, Figueiredo AC, Barroso JG, Ruberto G (1998) Antimicrobial and antioxidant properties of some commercial essential oils. Flavour Fragr J 13:235–240 Bassole IH, Lamien-Meda A, Bayala B, Obame LC, Ilboudo AJ, Franz C, Novak J, Nebie RC, Dicko MH (2011) Chemical composition and antimicrobial activity of Cymbopogon citratus and Cymbopogon giganteus essential oils alone and in combination. Phytomedicine 18(12):1070–1074 Cavalcanti ES, Morais SM, Lima MA (2004) Larvicidal activity of essential oils from Brazilian plants against Aedes aegypti L. Mem Inst Oswaldo Cruz 99:541–544 Cheel J, Theoduloz C, Rodríguez J, Schmeda-Hirschmann G (2005) Free radical scavengers and antioxidants from Lemongrass (Cymbopogon citratus (DC.) Stapf.). J Agric Food Chem 53(7):2511–2517 Cilek JE, Hallmon CF, Johnson R (2011) Efficacy of several commercially formulated essential oils against caged female Aedes albopictus and Culex quinquefasciatus when operationally applied via an automatic-timed insecticide application system. J Am Mosq Control Assoc 27(3):252–255 Costa CA, Bidinotto LT, Takahira RK, Salvadori DM, Barbisan LF, Costa M (2011) Cholesterol reduction and lack of genotoxic or toxic effects in mice after repeated 21-day oral intake of lemongrass (Cymbopogon citratus) essential oil. Food Chem Toxicol 49(9):2268–2272 Devi RC, Sim SM, Ismail R (2011) Spasmolytic effect of citral and extracts of Cymbopogon cit- ratus on isolated rabbit ileum. J Smooth Muscle Res 47(5):143–156 Figueirinha A, Cruz MT, Francisco V, Lopes MC, Batista MT (2010) Anti-inflammatory activity of Cymbopogon citratus leaf infusion in lipopolysaccharide-stimulated dendritic cells: contri- bution of the polyphenols. J Med Food 13:681–90 Faruq MO (1994) TLC technique in the component characterization and quality determination of Bangladeshi lemongrass oil (Cymbopogon citratus (DC) Stapf.). Bangladesh J Sci Ind Res 29:27–38 Francisco V, Figueirinha A, Neves BM, García-Rodríguez C, Lopes MC, Cruz MT, Batista MT (2011) Cymbopogon citratus as source of new and safe anti-inflammatory drugs: bio-guided assay using lipopolysaccharide-stimulated macrophages. J Ethnopharmacol 133:818–827 Gayathri K, Jayachandran KS, Vasanthi HR, Rajamanickam GV (2011) Cardioprotective effect of lemon grass as evidenced by biochemical and histopathological changes in experimentally induced cardiotoxicity. Hum Exp Toxicol 30:1073–1082 Guanasingh CB, Nagarajan S (1981) Flavonoids of Cymbopogon citratus. Indian J Pharma Sci 43:115

382 35 Lemongrass Henning SM, Zhang Y, Seeram NP, Lee RP, Wang P, Bowerman S, Heber D (2011) Antioxidant capacity and phytochemical content of herbs and spices in dry, fresh and blended herb paste form. Int J Food Sci Nutr 62:219–225 Khan MS, Ahmad I (2011) In vitro antifungal, anti-elastase and anti-keratinase activity of essential oils of Cinnamomum-, Syzygium- and Cymbopogon-species against Aspergillus fumigatus and Trichophyton rubrum. Phytomedicine 19(1):48–55 Koh PH, Mohd Mokhtar RA, Iqbal M (2012) Antioxidant potential of Cymbopogon citratus extract: alleviation of carbon tetrachloride-induced hepatic oxidative stress and toxicity. Hum Exp Toxicol 31(1):81–91 Kumar P, Mishra S, Malik A, Satya S (2011) Repellent, larvicidal and pupicidal properties of essential oils and their formulations against the housefly, Musca domestica. Med Vet Entomol 25(3):302–310 Lee HJ, Jeong HS, Kim DJ, Noh YH, Yuk DY, Hong JT (2008) Inhibitory effect of citral on NO production by suppression of iNOS expression and NF-kappa B activation in RAW264.7 cells. Arch Pharm Res 31(3):342–349 Leite JR, Seabra Mde L, Maluf E, Assolant K, Suchecki D, Tufik S, Klepacz S, Calil HM, Carlini EA (1986) Pharmacology of lemongrass (Cymbopogon citratus Stapf). III. Assessment of eventual toxic, hypnotic and anxiolytic effects on humans. J Ethnopharmacol 17(1):75–83 Matouschek BK, Stahl BE (1991) Phytochemical study of non volatile substances from Cymbopogon citratus (DC.) Stapf (Poaceae). Pharm Acta Helv 66:242–245 Mickiene R, Bakutis B, Baliukoniene V (2011) Antimicrobial activity of two essential oils. Ann Agric Environ Med 18(1):139–144 Miean KH, Mohamed S (2001) Flavonoid (myricetin, quercetin, kaempferol, luteolin, and apigenin) content of edible tropical plants. J Agric Food Chem 49:3106–3112 Nakamura Y, Miyamoto M, Murakami A, Ohigashi H, Osawa T, Uchida K (2003) A phase II detoxification enzyme inducer from lemongrass: identification of citral and involvement of elec- trophilic reaction in the enzyme induction. Biochem Biophys Res Commun 302(3):593–600 Orrego R, Leiva E, Cheel J (2009) Inhibitory effect of three C-glycosylflavonoids from Cymbopogon citratus (Lemongrass) on human low density lipoprotein oxidation. Molecules 14:3906–3913 Pereira RP, Fachinetto R, de Souza PA, Puntel RL, Santos da Silva GN, Heinzmann BM, Boschetti TK, Athayde ML, Bürger ME, Morel AF, Morsch VM, Rocha JB (2009) Antioxidant effects of different extracts from Melissa officinalis, Matricaria recutita and Cymbopogon citratus. Neurochem Res 34(5):973–983 Quintans-Junior L, da Rocha RF, Caregnato FF, Moreira JC, da Silva FA, Araujo AA, dos Santos JP, Melo MS, de Sousa DP, Bonjardim LR, Gelain DP (2011) Antinociceptive action and redox properties of citronellal, an essential oil present in lemongrass. J Med Food 14:630–639 Rabbani SI, Devi K, Khanam S, Zahra N (2006) Citral, a component of lemongrass oil inhibits the clastogenic effect of nickel chloride in mouse micronucleus test system. Pak J Pharm Sci 19(2):108–113 Rao BS, Shanbhoge R, Rao BN, Adiga SK, Upadhya D, Aithal BK, Kumar MR (2009) Preventive efficacy of hydroalcoholic extract of Cymbopogon citratus against radiation-induced DNA damage on V79 cells and free radical scavenging ability against radicals generated in vitro. Hum Exp Toxicol 28:195–202 Shah G, Shri R, Panchal V, Sharma N, Singh B, Mann AS (2011) Scientific basis for the therapeu- tic use of Cymbopogon citratus, stapf (Lemon grass). J Adv Pharm Technol Res 2(1):3–8 Sharma PR, Mondhe DM, Muthiah S, Pal HC, Shahi AK, Saxena AK, Qazi GN (2009) Anticancer activity of an essential oil from Cymbopogon flexuosus. Chem Biol Interact 179(2–3):160–168 Tapia A, Cheel J, Theoduloz C, Rodríguez J, Schmeda-Hirschmann G, Gerth A, Wilken D, Jordan M, Jiménez-González E, Gomez-Kosky R, Mendoza EQ (2007) Free radical scavengers from Cymbopogon citratus (DC.) stapf plants cultivated in bioreactors by the temporary immersion (TIS) principle. Z Naturforsch C 62(5-6):447–457

References 383 Tchoumbougnang F, Zollo PH, Dagne E, Mekonnen Y (2005) In vivo antimalarial activity of essential oils from Cymbopogon citratus and Ocimum gratissimum on mice infected with Plasmodium berghei. Planta Med 71:20–23 Tiwari M, Dwivedi UN, Kakkar P (2010) Suppression of oxidative stress and pro-inflammatory mediators by Cymbopogon citratus D. Stapf extract in lipopolysaccharide stimulated murine alveolar macrophages. Food Chem Toxicol 48:2913–2919 Viana GS, Vale TG, Pinho RS, Matos FJ (2000) Antinociceptive effect of the essential oil from Cymbopogon citratus in mice. J Ethnopharmacol 70:323–327 Viuda-Martos M, El Gendy AE, Sendra E, Fernandez-Lopez J, Abd El Razik KA, Omer EA, Perez-Alvarez JA (2010) Chemical composition and antioxidant and anti-listeria activities of essential oils obtained from some Egyptian plants. J Agric Food Chem 58:9063–9070 Wannissorn B, Jarikasem S, Siriwangchai T (2005) Antibacterial properties of essential oils from Thai medicinal plants. Fitoterapia 76:233–236

Chapter 36 Licorice Botanical Name: Glycyrrhiza glabra L. Synonyms: black sugar, licorice root, liquorice, sweet root, sweetwood, Russian licorice, Spanish licorice, Turkish licorice. Family: Fabaceae (Leguminosae). Common Names: French: regliss; German: Lakritze; Italian: liquirizia; Spanish: regaliz; Hindi: mulethi. Introduction History A papyrus dating back from the time of Roman Empire and Assyrian tablets describes the therapeutic value of licorice, and the root has also been mentioned in the first Chinese herbal. Hippocrates, Theophrastus, and Pliny all referred to licorice. Theophrastus (372–287 BC) wrote: “Liquorice has the property of quenching the thirst if held in the mouth. The root contains a special sweetness which is safe for diabetics”. The roots became popular chewing sticks in Italy, Spain, West Indies, and other places where the plant grows. The Greeks learned about the sweet root from the Scythians. Later, it became glycyrrhiza (glykys, meaning “sweet” and rhiza, “root”). It was widely cultivated in Italy in the fifteenth century, and also found its way into northern Europe. The Latin liquiritia turned into lycorys in Old French. The Dominican Black Friars introduced licorice into England, where lycorys extract was later sold as lozenges called “pomfrey cakes”. The monestary gardens of Pontefract grew licorice, which later became the licorice confectionary center of Britain. D.J. Charles, Antioxidant Properties of Spices, Herbs and Other Sources, 385 DOI 10.1007/978-1-4614-4310-0_36, © Springer Science+Business Media New York 2013

386 36 Licorice Producing Regions It is indigenous to southeastern Europe, Middle East, and northern India. It is extensively cultivated in Europe (Spain, Italy, France), Middle East (Iran, Iraq, Syria, Turkey), and Asia (China, India). Botanical Description It is a perennial herb or bushy herb up to 2 m (6 ft) high, with oblong leaves and small blue-violet flowers. The leaves are divided into several pairs of leaflets. The fruits are small, reddish pods. The rhizomes are grayish brown on the outside and yellow within, with a fibrous texture. There are several varieties and species of licorice-Spanish lico- rice (G. glabra L. var. typica Reg. et Herd.), Persian licorice (G. glabra L. var. violacea Boiss.), Russian licorice (G. glabra L. var. glandulifera Waldst. et Kit.), and Chinese licorice (G. uralensis Fisch.). Parts Used Dried root or rhizomes, or more commonly the hard black sticks formed from boiled root juice. Much of the licorice used in the USA is imported in an extract form, usu- ally in sticks or solid blocks. Flavor and Aroma Medicinal and very highly aromatic. Very sweet taste, similar to anise, with slightly bitter and salty aftertaste. Active Constituents Glycyrrhizin (5–10%), flavonoids, polysaccharides, chalcones, asparagine, cou- marins, saponins, sterols, tannins, starch (30%), sugars (14%), amino acids, amines, gums, and essential oils. Preparation and Consumption Licorice flavors candies, liqueurs, ice cream, chewing gum, and baked goods. Used as a tisane and to flavor syrups, dried fruit salads, and alcoholic drinks such as raki and sambucca. It is used in flavoring tobacco.

Medicinal Uses and Functional Properties 387 Medicinal Uses and Functional Properties It is commonly used as a demulcent, expectorant, antitussive, and mild laxative. In Chinese traditional medicine, it is used to treat ulcers (gastric and duodenal), sore throat, malaria, abdominal pain, insomnia, tuberculosis, sores, abscesses, and food poisoning. It has been used in many countries to treat cancer. They are used extensively as ingredients in cough drops and syrups, tonics, laxatives, antismoking lozenges. It is also used as flavoring agents to mask bitter, nauseous, or other undesirable tastes in certain medicines. Licorice has an ancient reputation as an aphrodisiac, the Kama Sutra and Ananga Ranga contain numerous recipes for increasing sexual vigor which include licorice. Flavonoids such as licoagrodin, licoagrochalcones, licoagroaurone and licochal- cone C, kanzonol Y, glyinflanin B and glycyrdione A from licorice root have shown various pharmacological activities including antitumor, antiparasitic, antileishma- nial, anti-ulcer, and antioxidative effects. Isoliquiritigenin a flavonoid isolated from the roots of licorice was found to relax the guinea pig trachea through a multiple of intracellular actions, including sGC activation, inhibition of PDEs, and associated activation of the cGMP/PKG signaling cascade, leading to the opening of large- conductance Ca2+-activated K+ channels (BKCa) and Ca2+ decrease through PKG- dependent mechanism and thus to tracheal relaxation (Liu et al. 2008). Glycyrrhizic acid (GA) and 18b-glycyrrhetinic acid (18bGA) from licorice root was found to significantly inhibit the production of lipopolysaccharide (LPS)-induced nitric oxide (NO), prostaglandin E(2) (PGE(2)), and intracellular reactive oxygen species (ROS). Both GA and 18bGA significantly reduced the protein and mRNA levels of iNOS and COX-2 in LPS-induced macrophages. They inhibited the activation of NF- B and the activities of phosphoinositide-3-kinase (P13K) p110d and p110g iso- forms and then reduced the production of LPS-induced tumor necrosis factor-a (TNF-a), interleukin (IL)-6, and IL-1b in a dose-dependent manner. These results suggest that both GA and 18bGA may provide an anti-inflammatory effect by atten- uating the generation of excessive NO, PGE(2), and ROS and by suppressing the expression of proinflammatory genes through the inhibition of NF-кB and P13K activity (Wang et al. 2011). Shetty et al. (2011) found 18a-glycyrrhetinic acid (AGA) to inhibit proliferation and growth of prostate cancer cell line DU-145 by inducing apoptosis. Both 18b-glycyrrhetinic acid (18bGA) and its derivative glycyrrhetinic acid-30-piperazine were found to have potent antimycobacterial properties against the drug-susceptible and drug-resistant Mycobacterium bovis (Zhou et al. 2011). GRA (18B-glycyrrhetinic acid from licorice root showed potent inhibitory effects on MCF-7 proliferation in a concentration- and time-dependent manner without affecting immortalized normal mammary epithelial cell line (MCF- 10A). The growth inhibition of MCF-7 cells by GRA occurred through apoptosis. Their results suggested that GRA induces apoptosis in human breast carcinoma MCF-7 cells via caspase activation and modulation of Akt/FOXO3a pathway (Sharma et al. 2012). Liquiritigenin, a main compound of licorice, effectively atten- uated the acute behavioral effects of cocaine exposure and prevented the induction

388 36 Licorice of selective neuroadaptive changes in dopaminergic signaling pathways in rats (Jang et al. 2011). Jhanji et al. (2011) demonstrated that isoliquiritigenin (ISL) from licorice extract had an antiangiogenic effect. Licorice as a dietary additive was found to be feasible for immune system enhancement (Katayama et al. 2011). Nettle and licorice extracts were found to stimulate cellular response and nonspecific resis- tance, with these effects being superior to those of pharmacopoeial Echinacea purpurea tincture (Borsuk et al. 2011). Oral administration of glycyrrhetinic acid, an active constituent of licorice, at a dose of 45 mg kg−1 body weight to hamsters treated with 7,12-dimethylbenz(a)anthracene was shown to completely prevent the tumor formation as well as restore the status of detoxification enzymes (Kowsalya et al. 2011). Glabridin, a flavonoid purified from licorice root, was reported to have good promise for use in preventing osteoclastogenesis by inhibiting RANKL- induced activation of signaling molecules and subsequent transcription factors in osteoclast precursors (Kim et al. 2012). The induction of mTOR-dependent autophagic and apoptotic cell death was found to be an important mechanism in cancer chemotherapy by isoliquiritigenin (ISL), a flavonoid isolated from licorice (Chen et al. 2012). The beneficial effects of licorice and its constituents for prevent- ing/treating oro-dental diseases have been also reported (Messier et al. 2012). Antioxidant Properties Compounds extracted from the roots and leaves of licorice have been shown to have antioxidant properties (Gordon and An 1995; Vaya et al. 1997; Fuhrman et al. 1997; Haraguchi et al. 1998; Belinky et al. 1998a, b; Biondi et al. 2003; Murcia et al. 2004; Kang et al. 2005; Chin et al. 2007; Kim et al. 2008; Mekseepralard et al. 2010; Mukherjee et al. 2010; Shi et al. 2010; Sun et al. 2010; Franceschelli et al. 2011; Hasanein 2011; Kataya et al. 2011; Li et al. 2011; Ni et al. 2011; Ojha et al. 2011; Sakr et al. 2011; Sen et al. 2011; Siracusa et al. 2011; Veratti et al. 2011; Visavadiya and Narasimhacharya 2011; Wu et al. 2011; Yehuda et al. 2011; Yin et al. 2011; Zhang et al. 2011; Gabriele et al. 2012; Lateef et al. 2012). Retrochalcones isolated from the roots of licorice were shown to be effective in protecting biological systems against various oxidative stresses (Haraguchi et al. 1998). Hispaglabridin A, his- paglabridin B, glabridin, 4¢-O-methylglabridin, isoprenylchalcone derivative, and isoliquiritigenin were found to be very potent antioxidants toward LDL oxidation with glabridin being the most abundant and potent antioxidant. These natural anti- oxidants may be beneficial to attenuate atherosclerosis as LDL oxidation is a key event in the formation of the early atherosclerosis lesion (Vaya et al. 1997). Licorice ethanolic extract and glabridin were shown to inhibit LDL oxidation by a mechanism involving scavenging of free radicals. Dietary supplementation of each E zero mouse with licorice or pure glabridin for 6 week resulted in a substantial reduction in the susceptibility of their LDL to oxidation along with a reduction in the atherosclerotic lesion area (Fuhrman et al. 1997). Belinky et al. (1998b) found that the antioxidant effect of glabridin on LDL oxidation resided mainly in the 2¢hydroxyl and that the

References 389 hydrophobic moiety of the isoflavan is essential to obtain this effect. Glabridin has also been shown to inhibit NO production and inducible nitric oxide (iNOS) gene expression in murine macrophages by blocking NF-kappaB/Rel activation and that this effect was mediated at least partly by inhibiting the reactive oxygen species gen- eration (Kang et al. 2005). Isoliquiritigenin (ILG) from licorice root was shown to inhibit LPS-induced NO and prostaglandin E(2) (PGE(2)) production. It was also found that the anti-inflammatory properties of ILG were caused by iNOS, cyclooxy- genase-2 (COX-2), TNF-alpha, and IL-6 downregulation due to NF-kappaB inhibi- tion via the suppression of IkappaB kinase (IKK), ERK1/2, and p38 phosphorylation in RAW 264.7 cells (Kim et al. 2008). Franceschelli et al. (2011) studied the antioxi- dant activity of licochalcone C at a concentration of 50 mM on THP-1 (human myel- omonocytic leukemia) cells treated with proinflammatory stimuli such as LPS and IFN-g. The results showed that treatment with licochalcone C attenuated the LPS- IFN-g-induced inflammatory response by significantly decreasing the expression and activity of iNOS via nuclear factor kappa-B (NF-kB), by influencing extracellular O2-production, and by modulating the antioxidant network activity of superoxide dismutase (SOD), catalase (CAT), and glutathione peroxidase (GPx) activity. They hypothesized that licochalcone C has antioxidant activity properties since it reduces the production of superoxide radicals and consequently reduces the activity of iNOS. Licorice was found to have cardioprotective potential against myocardial infarction of oxidative stress and favorable modulation of cardiac function (Ojha et al. 2011). Pretreatment of cisplatin-treated mice with GA prevented oxidative stress by restor- ing the levels of antioxidant enzymes at both doses. A significant dose-dependent decrease in DNA fragmentation, micronucleus formation (p < 0.05), and the kidney toxicity markers BUN (p < 0.001), creatinine (p < 0.01), and LDH (p < 0.001) and res- toration of normal kidney histology were observed. These results clearly support the claim that the phytochemical GA has the potential to attenuate the side effects of anticancer drug overdose (Arjumand and Sultana 2011). Licorice extract was shown to restore the total antioxidant capacity of diabetic rats. Thus licorice may have a potential therapeutic effect for diabetes due to its antioxidant and antihyperglycemic properties (Kataya et al. 2011). Huo et al. (2011) reported a chemopreventive poten- tial of licorice extract against liver oxidative injury. The cardioprotective potential of G. glabra against myocardial infarction by amelioration of oxidative stress and favor- able modulation of cardiac function was shown in rats (Ojha et al. 2011). References Arjumand W, Sultana S (2011) Glycyrrhizic acid: a phytochemical with a protective role against cisplatin-induced genotoxicity and nephrotoxicity. Life Sci 89:422–429 Belinky PA, Aviram M, Fuhrman B, Rosenblat M, Vaya J (1998a) The antioxidative effects of the isoflavan glabridin on endogenous constituents of LDL during its oxidation. Atherosclerosis 137:49–61 Belinky PA, Aviram M, Mahmood S, Vaya J (1998b) Structural aspects of the inhibitory effect of glabridin on LDL oxidation. Free Radic Biol Med 24:19–29

390 36 Licorice Biondi DM, Rocco C, Ruberto G (2003) New dihydrostilbene derivatives from the leaves of Glycyrrhiza glabra and evaluation of their antioxidant activity. J Nat Prod 66:477–480 Borsuk OS, Masnaya NV, Sherstoboev EY, Isaykina NV, Kalinkina GI, Reihart DV (2011) Effects of drugs of plant origin on the development of the immune response. Bull Exp Biol Med 151(2):194–196 Chen G, Hu X, Zhang W, Xu N, Wang FQ, Jia J, Zhang WF, Sun ZJ, Zhao YF (2012) Mammalian target of rapamycin regulates isoliquiritigenin-induced autophagic and apoptotic cell death in adenoid cystic carcinoma cells. Apoptosis 17(1):90–101 Chin Y-W, Jung HA, Liu Y, BN Su, Castoro JA, Keller WJ, Pereira MA, Kinghorn AD (2007) Anti-oxidant constituents of the roots and stolons of licorice (Glycyrrhiza glabra). J Agric Food Chem 55:4691–4697 Franceschelli S, Pesce M, Vinciguerra I, Ferrone A, Riccione G, Antonia P, Grilli A, Felaco M, Speranza L (2011) Licochalcone-C extracted from Glycyrrhiza glabra inhibits lipopolysaccha- ride-interferon-g inflammation by improving antioxidant conditions and regulating inducible nitric oxide synthase expression. Molecules 16:5720–5734 Fuhrman B, Buch S, Vaya J, Belinky PA, Coleman R, Hayek T, Aviram M (1997) Licorice extract and its major polyphenol glabridin protect low-density lipoprotein against lipid peroxidation: in vitro and ex vivo studies in humans and in atherosclerotic apolipoprotein E-deficient mice. Am J Clin Nutr 66:267–275 Gabriele B, Fazio A, Carchedi M, Plastina P (2012) In vitro antioxidant activity of extracts of Sybaris liquorice roots from Southern Italy. Nat Prod Res 0:1–6 Gordon MH, An J (1995) Antioxidant activity of flavonoids isolated from licorice. J Agric Food Chem 43:1784–1788 Haraguchi H, Ishikawa H, Mizutani K, Tamura Y, Kinoshita T (1998) Antioxidative and superox- ide scavenging activities of retrochalcones in Glycyrrhiza inflata. Bioorg Med Chem 6:339–347 Hasanein P (2011) Glabridin as a major active isoflavan from Glycyrrhiza glabra (licorice) reverses learning and memory deficits in diabetic rats. Acta Physiol Hung 98:221–230 Huo HZ, Wang B, Liang YK, Bao YY, Gu Y (2011) Hepatoprotective and antioxidant effects of lico- rice extract against CCl(4)-induced oxidative damage in rats. Int J Mol Sci 12(10): 6529–6543 Jang EY, Hwang M, Yoon SS, Lee JR, Kim KJ, Kim HC, Yang CH (2011) Liquiritigenin decreases selective molecular and behavioral effects of cocaine in rodents. Curr Neuropharmacol 9(1):30–34 Jhanji V, Liu H, Law K, Lee VY, Huang SF, Pang CP, Yam GH (2011) Isoliquiritigenin from lico- rice root suppressed neovascularisation in experimental ocular angiogenesis models. Br J Opthalmol 95(9):1309–1315 Kang JS, Yoon YD, Cho IJ, Han MH, Lee CW, Park SK, Kim HM (2005) Glabridin, an isoflavan from licorice root, inhibits inducible nitric-oxide synthase expression and improves survival of mice in experimental model of septic shock. J Pharmacol Exp Ther 312:1187–1194 Kataya HH, Hamza AA, Ramadan GA, Khasawneh MA (2011) Effect of licorice extract on the complications of diabetes nephropathy in rats. Drug Chem Toxicol 34:101–108 Katayama M, Okamura T, Suzuki E, Tamura K, Shimizu Y, Suda Y, Suzuki K (2011) Effect of dietary addition of seaweed and licorice on the immune performance of pigs. Anim Sci J 82(2):274–281 Kim JY, Park SJ, Yun KJ, Cho YW, Park HJ, Lee KT (2008) Isoliquiritigenin isolated from the roots of Glycyrrhiza uralensis inhibits LPS-induced iNOS and COX-2 expression via the atten- uation of NF-kappaB in RAW 264.7 macrophages. Eur J Pharmacol 584:175–184 Kim HS, Suh KS, Sul D, Kim BJ, Lee SK, Jung WW (2012) The inhibitory effect and the molecu- lar mechanism of glabridin on RANKL-induced osteoclastogenesis in RAW264.7 cells. Int J Mol Med 29(2):169–177 Kowsalya R, Vishwanathan P, Manoharan S (2011) Chemopreventive potential of 18beta-glycyr- rhetinic acid: an active constituent of liquorice, in 7,12-dimethylbenz(a)anthracene induced hamster buccal pouch carcinogenesis. Pak J Biol Sci 14(11):619–626

References 391 Lateef M, Iqbal L, Fatima N, Siddiqui K, Afza N, Zia-Ul-Haq M, Ahmad M (2012) Evaluation of antioxidant and urease inhibition activities of roots of Glycyrrhiza glabra. Pak J Pharm Sci 25(1):99–102 Li YJ, Chen J, Li Y, Li Q, Zheng YF, Fu Y, Li P (2011) Screening and characterization of natural antioxidants in four Glycyrrhiza species by liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry. J Chromatogr A 1218(45):8181–8191 Liu B, Yang J, Wen Q, Li Y (2008) Isoliquiritigenin, a flavonoid from licorice, relaxes guinea-pig tracheal smooth muscle in vitro and in vivo: role of cGMP/PKG pathway. Eur J Pharmacol 587(1–33):257–266 Mekseepralard C, Kamkaen N, Wilkinson JM (2010) Antimicrobial and antioxidant activities of traditional Thai herbal remedies for aphthous ulcers. Phytother Res 24:1514–1519 Messier C, Epifano F, Genovese S, Grenier D (2012) Licorice and its potential beneficial effects in common oro-dental diseases. Oral Dis 18(1):32–39 Mukherjee M, Bhaskaran N, Srinath R, Shivaprasad HN, Allan JJ, Shekhar D, Agarwal A (2010) Anti-ulcer and antioxidant activity of GutGard. Indian J Exp Biol 48:269–274 Murcia MA, Egea I, Romojaro F, Parras P, Jiménez AM, Martínez-Tomé M (2004) Antioxidant evaluation in dessert spices compared with common food additives. Influence of irradiation procedure. J Agric Food Chem 52:1872–1881 Ni YF, Kuai JK, Lu ZF, Yang GD, Fu HY, Wang J, Tian F, Yan XL, Zhao YC, Wang YJ, Jiang T (2011) Glycyrrhizin treatment is associated with attenuation of lipopolysaccharide-induced acute lung injury by inhibiting cyclooxygenase-2 and inducible nitric oxide synthase expres- sion. J Surg Res 165:e29–e35 Ojha S, Golechha M, Kumari S, Bhatia J, Arya DS (2011) Glycyrrhiza glabra protects from myo- cardial ischemia-reperfusion injury by improving hemodynamic, biochemical, histopathologi- cal and ventricular function. Exp Toxicol Pathol 08:011 Sakr S, El-Kenawy A, El-Sahra D (2011) Metiram-induced nephrotoxicity in albino mice: effect of licorice aqueous extract. Environ Toxicol 1002/tox.20728 Sen S, Roy M, Chakraborti AS (2011) Ameliorative effects of glycyrrhizin on streptozotocin- induced diabetes in rats. J Pharm Pharmacol 63:287–296 Sharma G, Kar S, Palit S, Das PK (2012) 18b-glycyrrhetinic acid induces apoptosis through modu- lation of Akt/FOXO3a/BIM pathway in human breast cancer MCF-7 cells. J Cell Physiol 227(5):1923–1931 Shetty AV, Thirugnanam S, Dakshinamoorthy G, Samykutty A, Zheng G, Chen A, Bosland MC, Kajdacsy-Balla A, Ganasekar M (2011) 18a-glycyrrhetinic acid targets prostate cancer cells by down-regulating inflammation-related genes. Int J Oncol 39:635–640 Shi JR, Mao LG, Jiang RA, Qian Y, Tang HF, Chen JQ (2010) Monoammonium glycyrrhizinate inhibited the inflammation of LPS-induced acute lung injury in mice. Int Immunopharmacol 10:1235–1241 Siracusa L, Saija A, Cristani M, Cimino F, D’Arrigo M, Trombetta D, Rao F, Ruberto G (2011) Phytocomplexes from liquorice (Glycyrrhiza glabra L.) leaves – chemical characterization and evaluation of their antioxidant, anti-genotoxic and anti-inflammatory activity. Fitoterapia 82:546–556 Sun YX, Tang Y, Wu AL, Liu T, Dai XL, Zheng QS, Wang ZB (2010) Neuroprotective effect of liquiritin against focal cerebral ischemia/reperfusion in mice via its antioxidant and antiapop- tosis properties. J Asian Nat Prod Res 12:1051–1060 Vaya J, Belinky PA, Aviram M (1997) Antioxidant constituents from licorice roots: isolation, struc- ture elucidation and antioxidative capacity toward LDL oxidation. Free Radic Biol Med 23:302–313 Veratti E, Rossi T, Giudice S, Benassi L, Bertazzoni G, Morini D, Azzoni P, Bruni E, Giannetti A, Magnoni C (2011) 18(beta)-glycyrrhetinic acid and glabridin prevent oxidative DNA fragmen- tation in UVB-irradiated human keratinocyte cultures. Anticancer Res 31:2209–2215 Visavadiya NP, Narasimhacharya AV (2011) Ameliorative effects of herbal combinations in hyperlipidemia. Oxid Med Cell Longev 2011:160408

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Chapter 37 Marjoram Sweet Botanical Name: Origanum majorana L. Synonyms: Majorana hortensis; knotted marjoram. Family: Lamiaceae (Labiatae). Common Names: French: Marjolaine; German: Majoran; Italian: Maggiorana; Spanish: Mejorana. Introduction History Marjoram Sweet was known to the ancient Egyptians, Greeks and Romans and was grown in Egypt over 3,000 years ago. It was cultivated as a pot herb and used to flavor food. It was also prized as a miracle herb with the power to cure all diseases, especially colds and chills. The ancient Greeks and Romans crowned newlyweds with marjoram as a symbol of happiness. The Greeks called marjoram “joy of the mountains”, and wore marjoram wreaths at weddings. The Greeks used it as a sym- bol of happiness, and believed that if placed or grown near the grave, the dead would enjoy eternal peace and happiness. They also believed that if the girl placed marjo- ram on her bed, Aphrodite would visit her in dreams and reveal the identity of her husband. Sweet marjoram to this day remains on the coat of arms of the ancient city of Marjora from which it gets its name. In Crete, it was worn by distinguished lead- ers as a badge of honor. It was used in houses to give a clean, pleasant smell, and in linen cupboards. It was popular in the Middle Ages as a medicinal herb, and as a culinary herb during the sixteenth century in England. According to Banckes’s Herbal, marjoram would cure a cold if it was bound on the head; it was also good for bronchial coughs, asthmatic whooping coughs, and other respiratory ailments. D.J. Charles, Antioxidant Properties of Spices, Herbs and Other Sources, 393 DOI 10.1007/978-1-4614-4310-0_37, © Springer Science+Business Media New York 2013

394 37 Marjoram Sweet Producing Regions Marjoram is native to the Mediterranean region and is now grown in Hungary, Germany, USA, France, Spain, Portugal, UK, North Africa, and west Asia. The oil is mostly produced in Morocco, France, Tunisia, Egypt, Bulgaria, Germany, and Hungary. Botanical Description It is a herbaceous plant up to 0.6 m (1–2 ft) high. It is a perennial bushy plant, but annual or biennial in Europe. It has oblique rhizome, hairy shrub like stalks, oppo- site dark green oval leaves, and white or red flowers in clustered bracts. The leaves are whole, larger ones being fragmented, oblate to broadly elliptical. The plant is highly aromatic. The dried herb is light green with a slight grayish tint. Parts Used The fresh leaves are used whole or chopped. They are used as garnish and in salads. The dried leaves are used whole, cut or ground. Essential oils and oleoresins. The aromatic seeds are employed in French confitures and confectionery. Flavor and Aroma It has a pleasant, aromatic, and spicy aroma. It has fresh, spicy, bitter and slightly pungent, camphor-like notes. It has delicate, sweet aroma of sweet basil and thyme and has fragrant, spicy, minty-sweet, slightly sharp, with bitter and camphoraceous undertones. Active Constituents The active constituents include Moisture 8%, protein 14%, fixed oil 5.6%, fiber 22%, ash 6–24%, and essential oil 1.8%. Other compounds are flavonoid glyco- sides, tannins, steroids, and vitamins (especially A and C). The major constituents of the essential oil are terpin-4-ol (20%), g-terpinene (20%), sabinene hydrate (12–15%), a-terpineol, sabinene, and linalool. The major phenolic acids are sinapic, ferulic, coumarinic, caffeic, syringic, vanillic, and 4-hydroxybenzoic acid (Petr et al. 2008). The nutritional constituents (dried) and ORAC (fresh) values of marjoram are given in Table 37.1.

Preparation and Consumption 395 Table 37.1 Nutrient composition and ORAC values of marjoram dried Nutrient Units Value per 100 g Water g 7.64 Energy kcal 271 Protein g 12.66 Total lipid (fat) g Carbohydrate, by difference g 7.04 Fiber, total dietary g 60.56 Sugars, total g 40.3 Calcium, Ca mg 4.09 Vitamin C, total ascorbic acid mg 1,990 Vitamin B-6 mg 51.4 Vitamin B-12 mcg 1.190 Vitamin A, RAE mcg_RAE 0.00 Vitamin A, IU IU 403 Vitamin D IU 8,068 Vitamin E (alpha-tocopherol) mg 0 Fatty acids, total saturated g 1.69 Fatty acids, total monounsaturated g 0.529 Fatty acids, total polyunsaturated g 0.940 4.405 Marjoram fresh mmol TE/100 g 27,297 H-ORAC mmol TE/100 g 27,297 Total-ORAC mg GAE/100 g TP 964 Source: USDA National Nutrient Database for Standard Reference, Release 24 (2011) Preparation and Consumption It is used for its well-rounded herb note. Marjoram may be used in sausages, lamb, mutton, beef, pork, chicken, fish, sea food, tomato dishes, soups, stews, stuffing’s, breads, salad dressings, and chowders. The widest use is in seasoning sausages and salamis. Marjoram is used in Italian, French, North African, Middle Eastern, and American cuisines and spice blends such as bouquet garni, fines herbs, and sausage and pickle blends. Marjoram is usually added towards the end of cooking. In European dishes it is added to fish sauces, butter-based sauces, salads, vinegar, eggplant, and mushroom sauces. In North Africa and Middle East, it is used in mut- ton, lamb, barbecues, vegetables, and seafood. In the USA, marjoram is mostly used in poultry seasonings, cheeses, sausages, soups, and salad dressings. The oil is used to flavor fats, oils, baked foods, meat products, processed vegetables, soups, vinegars, snack foods, and gravies.

396 37 Marjoram Sweet Medicinal Uses and Functional Properties It is considered antiseptic, antidiabetic, carminative, antispasmodic, stimulant, diaphoretic, and diuretic (Parry 1969; Rau et al. 2006) and is used as a tonic and cure for asthma, coughs, indigestion, rheumatism, headaches, and toothaches. It has also been used to treat cancers (Esiyok et al. 2004). The MIC for the fungi S. cerevisiae, C. paracrusei, C. krusei, and A. oryzae was <4.0% (Ueda et al. 1982). Marjoram inhibited the fungi A. fumigatus and A. niger (Yadava and Saini 1991; Tiziana and Dorman 1998). Marjoram oil was most effec- tive against Acinetobacter calcoaceticus, Vibio natriegens, and S. aureus (Tiziana and Dorman 1998). Marjoram extract was found to exhibit protective effect against hydroquinone-induced clastogenicity (Ghaly et al. 2008). Marjoram oil showed both bacteriostatic and bactericidal effects when applied to fresh sausage (Busatta et al. 2008). Essential oil of marjoram was shown to have antimicrobial activity against both Gram-positive and Gram-negative bacteria (Deans and Svoboda 1990; Barbosa et al. 2009). It was found to have a strong fumigant toxicity against Mediterranean flour moth (Karaborklu et al. 2011). Marjoram was shown to have strong antimicrobial activity (Ozcan et al. 2006; Leeja and Thoppil 2007; Sagdic et al. 2010). Antioxidant Properties Marjoram is also known to possess various therapeutic properties including antioxi- dant activity (Dapkevicius et al. 1997; Zheng and Wang 2001; Campanella et al. 2003; Dorman et al. 2004; Vagi et al. 2005; Tsai et al. 2007; Lopez et al. 2007; Yazdanparast and Shahriyary 2008; Al-Howiriny et al. 2009; Abdel-Massih et al. 2010; Celik et al. 2010; Viuda-Martos et al. 2010; Shati 2011; Mossa and Nawwar 2011; Hossain et al. 2012). Saito et al. (1976) reported higher antioxidant activity of marjoram at 0.02% against lard than tocopherol. In the egg yolk assay, the antioxi- dant activity of marjoram was found to be much higher than that of a-tocopherol and comparable with BHT at all concentrations tested (Tiziana and Dorman 1998). Nakatani (2000) studied the compounds from various herbs and spices for their antioxidant activity and isolated 26 active compounds from marjoram, rosemary, thyme, and oregano. Sweet marjoram aqueous extract was shown to have a remark- able capacity in retarding lipid oxidation, and these extracts were found to be rich in bound forms of phenolic compounds such as hydroxycinnamic acids and flavonoids (Triantaphyllou et al. 2001). Heo et al. (2002) found ursolic acid from marjoram to reduce the micromolar Abeta-induced oxidative cell death. Ursolic acid activity was assessed by MTT, lactate dehydrogenase, and trypan blue assay. El-Ashmawy et al. (2005) concluded from their study that marjoram plays an important role in amelio- rating liver and kidney functions and genotoxicity induced by lead toxicity. They found the essential oil, alcoholic, and aqueous extracts of marjoram to significantly reduce the serum activities of alanine and aspartate transaminases, alkaline

References 397 phosphatase, urea, and creatinine and improved the kidney and liver histology in comparison with lead acetate treated group. The essential oil of marjoram was able to reduce the damaging effects of ethanol toxicity on male fertility, liver, and brain tissues (El-Ashmawy et al. 2007). Dearlove et al. (2008) studied the effect of poly- phenolic substances of commercial culinary herbs including marjoram on fructose- mediated protein glycation. They found these extracts to be potent inhibitors of protein glycation and this is an example of the antidiabetic potential of these culi- nary herbs and spices. Marjoram ethanol extract was found to significantly decrease the incidence of ulcers, basal gastric secretion and acid output, and the concentra- tion of malondialdehyde (Al-Howiriny et al. 2009). Marjoram extract was shown to alleviate the kidney and liver antioxidant activities and lower the LPO levels that were disrupted by Cd in albino rats. Marjoram showed both protective and curative effects on Cd-induced hepatotoxicity and nephrotoxicity (Shati 2011). Regulatory Status GRAS 182.10 and GRAS 182.20. Standard ISO 10620. References Abdel-Massih RM, Fares R, Bazzi S, El-Chami N, Baydoun E (2010) The apoptotic and anti- proliferative activity of Origanum majorana extracts on human leukemic cell line. Leuk Res 34(8):1052–1056 Al-Howiriny T, Alsheikh A, Alqasoumi S, Al-Yahya M, ElTahir K, Rafatullah S (2009) Protective effect of Origanum majorana L. ‘Marjoram’ on various models of gastric mucosal injury in rats. Am J Chin Med 37(3):531–545 Barbosa LN, Rall VL, Fernandes AA, Ushimaru PI, da Silva PI, Fernandes A Jr (2009) Essential oils against foodborne pathogens and spoilage bacteria in minced meat. Foodborne Pathog Dis 6(6):725–728 Busatta C, Vidal RS, Popiolski AS, Mossi AJ, Dariva C, Rodrigues MR, Corazza FC, Corazza ML, Vladimir Oliveira J, Cansian RL (2008) Application of Origanum majorana L. essential oil as an antimicrobial agent in sausage. Food Microbiol 25(1):207–211 Campanella L, Bonanni A, Favero G, Tomassetti M (2003) Determination of antioxidant proper- ties of aromatic herbs, olives and fresh fruit using an enzymatic sensor. Anal Bioanal Chem 375(8):1011–1016 Celik SE, Ozyürek M, Guclü K, Apak R (2010) Determination of antioxidants by a novel on-line HPLC-cupric reducing antioxidant capacity (CUPRAC) assay with post-column detection. Anal Chim Acta 674(1):79–88

398 37 Marjoram Sweet Dapkevicius A, Venskutonis R, Van Beek TA, Linssen JPH (1997) Antioxidant activity of extracts obtained by different isolation procedures from some aromatic herbs grown in Lithuania. J Sci Food Agric 77:140–146 Deans SG, Svoboda KP (1990) The anti microbial properties of marjoram (Origanum majorana L.) volatile oil. Flavor Fragr J 5:187–190 Dearlove RP, Greenspan P, Hartle DK, Swanson RB, Hargrove JL (2008) Inhibition of protein glycation by extracts of culinary herbs and spices. J Med Food 11(2):275–281 Dorman HJ, Bachmayer O, Kosar M, Hiltunen R (2004) Antioxidant properties of aqueous extracts from selected lamiaceae species grown in Turkey. J Agric Food Chem 52(4):762–770 El-Ashmawy IM, El-Nahas AF, Salama OM (2005) Protective effect of volatile oil, alcoholic and aqueous extracts of Origanum majorana on lead acetate toxicity in mice. Basic Clin Pharmacol Toxicol 97(4):238–243 El-Ashmawy IM, Saleh A, Salama OM (2007) Effects of marjoram volatile oil and grape seed extract on ethanol toxicity in male rats. Basic Clin Pharmacol Toxicol 101(5):320–327 Esiyok D, Otles S, Akcicek E (2004) Herbs as a food source in Turkey. Asian Pac J Cancer Prev 5(3):334–339 Ghaly IS, Said A, Abdel-Wahhab MA (2008) Zizyphus jujuba and Origanum majorana extracts protect against hydroquinone-induced clastogenicity. Environ Toxicol Pharmacol 25(1):10–19 Heo HJ, Cho HY, Hong B, Kim HK, Heo TR, Kim EK, Kim SK, Kim CJ, Shin DH (2002) Ursolic acid of Origanum majorana L. reduces Abeta-induced oxidative injury. Mol Cells 13(1):5–11 Hossain MB, Brunton NP, Patras A, Tiwari B, O’Donnell CP, Martin-Diana AB, Barry-Ryan C (2012) Optimization of ultrasound assisted extraction of antioxidant compounds from marjo- ram (Origanum majorana L.) using response surface methodology. Ultrason Sonochem 19(3):582–590 Karaborklu S, Ayvaz A, Yilmaz S, Akbulut M (2011) Chemical composition and fumigant toxicity of some essential oils against Ephestia kuehniella. J Econ Entomol 104:1212–1219 Leeja L, Thoppil JE (2007) Antimicrobial activity of methanol extract of Origanum majorana L. (Sweet marjoram). J Environ Biol 28(1):145–146 Lopez V, Akerreta S, Casanova E, García-Mina JM, Cavero RY, Calvo MI (2007) In vitro antioxi- dant and anti-rhizopus activities of Lamiaceae herbal extracts. Plant Foods Hum Nutr 62(4):151–155 Mossa AT, Nawwar GA (2011) Free radical scavenging and antiacetylcholinesterase activities of Origanum majorana L. essential oil. Hum Exp Toxicol 30(10):1501–1513 Nakatani N (2000) Phenolic antioxidants from herbs and spices. Biofactors 13(1-4):141–146 Ozcan MM, Sagdic O, Ozkan G (2006) Inhibitory effects of spice essential oils on the growth of Bacillus species. J Med Food 9(3):418–421 Parry JW (1969) Spices, vol 1. Chemical Pub., Brooklyn, NY Petr J, Vítková K, Ranc V, Znaleziona J, Maier V, Knob R, Sevcík J (2008) Determination of some phenolic acids in Majorana hortensis by capillary electrophoresis with online electrokinetic preconcentration. J Agric Food Chem 56(11):3940–3944 Rau O, Wurglics M, Dingermann T, Abdel-Tawab M, Schubert-Zsilavecz M (2006) Screening of herbal extracts for activation of the human peroxisome proliferator-activated receptor. Pharmazie 61(11):952–956 Sagdic O, Ozturk I, Bayram O, Kesmen Z, Yilmaz MT (2010) Characterization of butter spoiling yeasts and their inhibition by some spices. J Food Sci 75(9):M597–M603 Shati AA (2011) Effects of Origanum majorana L. on cadmium induced hepatotoxicity and neph- rotoxicity in albino rats. Saudi Med J 32(8):797–805 Tiziana BM, Dorman DHJ (1998) Antimicrobial and antioxidant properties of some commercial oleoresin. Flavor Fragr J 13:235–244 Triantaphyllou K, Blekas G, Boskou D (2001) Antioxidative properties of water extracts obtained from herbs of the species Lamiaceae. Int J Food Sci Nutr 52(4):313–317 Tsai PJ, Tsai TH, Yu CH, Ho SC (2007) Evaluation of NO-suppressing activity of several Mediterranean culinary spices. Food Chem Toxicol 45(3):440–447

References 399 Ueda S, Yamashita H, Nakalima M, Kuwahara S (1982) Inhibition of microorganisms by spice extracts and flavouring compounds. Nippon Shokuhin Kogyo Gakkaishi 29:111 Vagi E, Rapavi E, Hadolin M, Vasarhelyine Peredi K, Balazs A, Blazovics A, Simandi B (2005) Phenolic and triterpenoid antioxidants from Origanum majorana L. herb and extracts obtained with different solvents. J Agric Food Chem 53(1):17–21 Viuda-Martos M, El Gendy AE, Sendra E, Fernandez-Lopez J, Abd El Razik KA, Omer EA, Perez-Alvarez JA (2010) Chemical composition and antioxidant and anti-Listeria activities of essential oils obtained from some Egyptian plants. J Agric Food Chem 58(16):9063–9070 Yadava RN, Saini VK (1991) Antimicrobial efficacy of essential oils of Majorana hortensis Moench and Anisomeles indica (L.) Kunteze. Indian Perfum 35(1):58–60 Yazdanparast R, Shahriyary L (2008) Comparative effects of Artemisia dracunculus, Satureja hortensis and Origanum majorana on inhibition of blood platelet adhesion, aggregation and secretion. Vascul Pharmacol 48(1):32–37 Zheng W, Wang SY (2001) Antioxidant activity and phenolic compounds in selected herbs. J Agric Food Chem 49(11):5165–5170

Chapter 38 Mustard Botanical Names: Brassica juncea (L.) Czernov. var. rugosa Bailey (Indian mustard, Chinese mustard, large-leaf mustard; brown or Synonyms: oriental mustard); Brassica nigra (L.) W.D.J. Koch (Black Family: mustard); Sinapis alba L. (White mustard, yellow mustard). Common Names: Synapsis juncea L.; B. rugosa Prain.; B. alba (L.) Rabenh.; B. alba (L.) Boiss.; B. hirta Moench. Brassicaceae (Cruciferae). French: Moutarde, moutarde noir, moutarde blanc; German: rutensenf or sareptasenf, schwartzen senf, weiber senf or senfsaat; Italian: senape Indiana, senape negra, senape bianca; Spanish: mostaza de Indias, mostaza negra, mostaza sivestre; Hindi: rai, raya, laha, banarsi rai. Introduction History The generally accepted name of mustard is believed to be derived from the Latin mustum ardens, meaning burning must, since the seed was sometimes ground with grape must. It is among the oldest recorded spices as seen in Sanskrit records dating to 3000 BC. Reference on Sumerian clay tablets of 2000 BC has a proverb: “When a poor man has died, do not try to revive him!/For when he had bread he had no salt/ And when he had salt he had no bread./When he had meat he had no mustard/And when he had mustard he had no meat”. Salt and mustard were the major Sumerian condiments. India was a major producer of mustard and still remains so today. The earliest reference to mustard in Chinese literature was related to B. japonica; appar- ently the true mustard was introduced much later from India along the Spice Road. A poultice of fennel, seeds of Vitex, Juniperus excelsa, tamarisk, tragacanth, asafoetida, D.J. Charles, Antioxidant Properties of Spices, Herbs and Other Sources, 401 DOI 10.1007/978-1-4614-4310-0_38, © Springer Science+Business Media New York 2013

402 38 Mustard Lolium and mint, mixed with flour, boiled in mustard water, and bandaged on the patient relieved pain. The Greeks and Romans ate the young green plants as a vegetable and mustard was used by the Europeans as a spice for thousands of years. The famous Greek philosopher, Pythagoras (503 BC), recommended a mustard poultice to treat scorpion stings, while another Greek, Hippocrates, some 100 years later, listed a number of internal and external medical uses for mustard seeds. Mustard seeds were used to entomb the kings in Egypt. The Roman Emperor Diocletian fixed the price of mustard seeds in AD 301, since it was such an impor- tant crop. There is an interesting story of the exchange between King Darius the third of Persia and Alexander the Great. King Darius sent a bag of sesame seeds to Alexander the Great symbolizing his vast army, who in turn replied with a bag of mustard seed to signify not only the equal number of his soldiers, but also their powerful energy. Mustard is mentioned in the Bible (Matthew 13: 31–32): 31 “The Kingdom of Heaven is like to a grain of mustard seed, which a man took, and sowed in his field:” 32 “Which indeed is the least of all seeds: but when it is grown, it is the greatest among herb and becometh a tree, so that the birds of the air come and lodge in the branches thereof”. It is also mentioned in Luke 17: 6; Luke 13: 19; Mark 4: 31; Matthew 17: 20. In the tenth century it was grown by the monks of St Germain des Pres near Paris, France. Guests at the fete given by the French Duke of Burgundy in 1336 are reported to have consumed 70 gallons of mustard in one sitting. Dijon, in France, still remains to this day a market leader in specialized mustard prepara- tions, and in 1634 the town was granted the exclusive right to make mustard. Today, Dijon mustard accounts for more than half the world’s mustard. In 1777, M. Grey and M. Poupon produced a strong, canary-yellow paste to a secret recipe which included white wine—it is still produced in attractive jars and bottles. Mustard was introduced to England by the Romans, and Tewkesbury was the famous mustard center of England. It is referred to in Shakespeare’s Henry IV Part 2, as: “His wit’s as thick as Tewkesbury mustard”. A set of Dame Alice de Bryene’s household accounts for the year 1418–1419 shows that she used 84 pounds of mustard seed bought for one farthing per pound from Stourbridge Fair. A description of contemporary mustard preparation is given in Delights for Ladies, written by Sir Hugh Plat and published in the seventeenth century. In the eighteenth century, Mrs. Clements of Durham became famous for Durham Mustard. By the nineteenth century, Mr. Jeremiah Coleman became famous and rich with his Colman mustard, and produced the famous saying, “It’s not the mustard that people eat that made Colman rich, but that left on the plate”. From the eighteenth century onwards, different mus- tard types were produced and became very famous. Mustard seeds were a symbol of fertility for the ancient Indians and have been used by Africans, Chinese, Greeks, and Indians since ancient times. Producing Regions B. juncea or brown mustard probably originated in Africa, but is widely cultivated from Eastern Europe to China and Japan. In Asia, it is a very important vegetable and

Introduction 403 oilseed crop. B. nigra or black mustard most probably originated in the region from W. Asia to Iran, it now occurs wild in the Mediterranean region, and throughout central Europe, the Middle East and the Ethiopian highlands. It is naturalized in the USA and parts of Britain. S. alba or white mustard is naturalized in England, the USA, and elsewhere. It is native to the Mediterranean region and W. Asia. It is grown commercially in eastern and northern Europe, and Canadian prairies. The major countries growing mustard are Nepal, India, Indonesia, Japan, Canada, USA, Russia, Great Britain, Italy, Czech Republic, Romania, Slovakia, Germany, and France. Botanical Description Brown mustard is an erect annual herb up to 1.5 m (3 ft) high, with grass-green vari- able leaves, small yellow flowers, and pungent brown seeds. Black mustard is a tall annual, branched herb up to 3 m (9 ft) high, with alternate mid-green pungent leaves, small yellow flowers, and small blackish seeds. White mustard is an annual herb up to 1.2 m (3 ft) high, with alternate, oval, mid to dull green leaves, yellow flowers, and pungent creamy seeds. Parts Used Seed (black, brown or uniform creamy) (whole or ground), oil. The seeds are used whole, crushed, ground, or as flour. It also comes in paste forms with water, vinegar, sugar, oil, spices, and herbs called prepared mustard. Mustard seed oil is pale yel- low. Mustard leaves are called mustard greens and are used as prepared vegetable or are used in salads. The most common mustard green comes from the brown mustard. Flavor and Aroma Sharp, fresh, pungent. Fresh, pungent, slightly biting flavor. The white or yellow mustard is largest and has delicate flavor and is the least burning. The brown mus- tard seed has a nutty, sweet, and mellow flavor. The black mustard seed has the sharpest flavor and a nutty aftertaste. Active Constituents All three types have almost similar composition. Average seed contains moisture 8%, protein 29%, fat 28%, carbohydrates 19%, fiber 11%, ash 5% (Ca, P, Fe),

404 38 Mustard Table 38.1 Nutrient composition and ORAC values of mustard seed ground Nutrient Units Value per 100 g Water g 5.27 Energy kcal 508 Protein g 26.08 Total lipid (fat) g 36.24 Carbohydrate, by difference g 28.09 Fiber, total dietary g 12.2 Sugars, total g 6.79 Calcium, Ca mg 266 Vitamin C, total ascorbic acid mg 7.1 Vitamin B6 mg 0.397 Vitamin B12 mcg 0.00 Vitamin A, RAE mcg_RAE 2 Vitamin A, IU IU 31 Vitamin D IU 0 Vitamin E (alpha-tocopherol) mg 5.07 Fatty acids, total saturated g 1.989 Fatty acids, total monounsaturated g 22.518 Fatty acids, total polyunsaturated g 10.088 H-ORAC mmol TE/100 g 28,759 L-ORAC mmol TE/100 g 498 Total-ORAC mmol TE/100 g 29,257 TP mg GAE/100 g 1,844 Source: USDA National Nutrient Database for Standard Reference, Release 24 (2011) b-carotene, thiamine, riboflavin, niacin, essential oil 1% (mainly allyl isothiocya- nate—90%), and glucosinolate sinigrin. Sinigrin on hydrolysis by myrosinase yields allyl isothiocyanate, glucose, and potassium bisulfate. The nutritional constituents and ORAC values of ground mustard seed are given in Table 38.1. Preparation and Consumption Tender green plants as well as green pods are eaten as vegetables or salads. Mustard greens have a radish-like biting taste. The British enjoy brown mustard with roast beef and ham. The Japanese use the oriental brown variety as a dip for raw fish. In the Caribbean, yellow or brown mustard is used with fruits and chili peppers for tasty sauces, marinades and stews. In Indian cooking, whole brown or black mustard seeds are “popped” or “tarkared” in heated ghee or oil, and then added to sauces, chutneys, pickles, curries, sambhars and dhals, to bring out the nutty flavor and aroma. Ground mustard or mustard flour is used in seafood, cocktail sauces, barbecue, sauces, cheese dishes, spice cakes and cookies, devilled eggs, baked beans, ham dishes, pork roast, ham salad, salad dressings, chowders, and bisques.

Medicinal Uses and Functional Properties 405 In Bengali fish dishes and curries, ground mustard provides flavor and consistency. Whole yellow mustard seeds are used in pickled condiments, while the paste form is popular for salad dressings and hot sauces. A variety of famous mustard blends are available: American ballpark-style mustard is from the white seeds and blended with sugar and wine or vinegar, colored with turmeric. It flavors hot dogs, ham, and barbecue relishes. Bordeaux mustard is made from black seeds, blended with unfermented wine. The seeds are not husked, thus giving a strong, aromatic, dark brown mustard often flavored with tarragon. This is good with sausages, cold meats, and in beer-flavored stews. Dijon mustard is light in color and made from husked black seeds or brown seeds blended with wine, salt, and spices. This mustard is used in classic French mustard sauces, salad dressings, and mayonnaise. It is sharp and salty, pungent, hot, but less than English mustard. Is used in classic French cuisine with steak and other grilled or roasted meats, especially rabbit. The famous French brands are Amora, Grey-poupon, Dijon, and Louti from Bordeaux. English mustard is hot and made from white seeds and sometimes mixed with wheat flour and turmeric for color. This accompanies beef, ham, gammon, or bacon, pork (especially sausages); it is an ingredient in Welsh rarebit and spicy sauces for fish and vegetables and also an ingredient in piccalilli relish. German mustard is generally a smooth blend of vinegar and black mustard, vary- ing in strength. It is slightly dark, sweet–sour, and flavored with herbs and spices. Uses same as Bordeaux mustard. Meaux mustard is yellow brown in color, made with the partly crushed, partly ground black seed mixed with vinegar, producing crunchy hot mustard for bland foods. Medicinal Uses and Functional Properties It has been used as a laxative, for the treatment of asthma, and to induce vomiting or relieve coughs. Mustard is considered diuretic, appetizer, emetic, rubefacient, and stimulant. It relieves congestion, neuralgia, and spasms. Used externally for treating rheumatism, arthritis, and lumbago. The consumption of low amounts of isothiocyanates (ITC)-containing mustard was found to quickly and effectively modulate the cytoprotective factors in peripheral blood mononuclear cells and/or blood. The fact that these observations were confirmed by two cytogenetic biomark- ers for cancer risk implies that even short-term intake of ITC-containing vegetables might indeed be associated with reduced cancer risk (Lamy et al. 2012). Sinigrin, a major glucosinolate present in Indian mustard (Brassica juncea L.) seeds, acts as the precursor of the anticancer compound allyl isothiocyanate, and shows a wide range of biological activities (Wang et al. 2011). In an orthotopic rat bladder cancer model, oral allyl isothiocyanate (AITC)-rich mustard seed powder (MSP-1) at 71.5 mg kg−1 (sinigrin dose of 9 mmol kg−1) inhibited bladder cancer growth by

406 38 Mustard 34.5% (P < 0.05) and blocked muscle invasion by 100%. Moreover, the anticancer activity was associated with significant modulation of key cancer therapeutic targets, including vascular endothelial growth factor, cyclin B1, and caspase 3. On an equimolar basis, the anticancer activity of (AITC) delivered as MSP-1 appears to be more robust than that of pure AITC. MSP-1 was thus shown to be an attractive delivery vehicle for AITC and it strongly inhibits bladder cancer development and progression (Bhattacharya et al. 2010). Antioxidant Properties Mustard seed and leaves have been reported to have antioxidant properties (Kim et al. 2002, 2003; Yokozawa et al. 2002, 2003; Choi et al. 2002; Gagandeep et al. 2005; Tiku et al. 2008; Benson and Devi 2009; Jung et al. 2009; Lee et al. 2010; Gill et al. 2011; Khattak 2011; Yuan et al. 2011). A new kaempferol 7-O-triglucoside (7-O-beta-d-glucopyranosyl-(1→3)-[beta-d-glucopyranosyl-(1→6)]- glucopyranoside) isolated from the leaves of mustard was found to be a scavenger of 1,1-diphenyl-2-picrylhydrazyl radical (Kim et al. 2002). The radical scavenging isorhamnetin 7-O-glucoside isolated from mustard leaves showed the peroxynitrite and DPPH scavenging activities with IC50 values of 2.07 ± 0.17 and 13.3 mM (Choi et al. 2002). Yokozawa et al. (2002) showed that isorhamnetin diglucoside is metab- olized in vivo by intestinal bacteria to isorhamnetin and that isorhamnetin plays an important role as an antioxidant. The BuOH fraction of mustard leaf was found to control glucose metabolism and reduce lipid peroxidation as well as the level of oxygen radicals, ameliorating the damage caused by oxidative stress in diabetes (Kim et al. 2003). An EtOAc fraction from mustard leaves was found to have strong inhibitory effects, which was concentration-dependent, on the formation of advanced glycation end products and free radical-mediated protein damage in an in vitro system, indicating that this fraction has a potential protective role against diabetes and/or its complications (Yokozawa et al. 2003). Mustard seeds were suggested to have strong cancer chemopreventive potentials and their ability to enhance antioxidant defence system and then in turn to provide protection against the toxic effects of carcinogens (Gagandeep et al. 2005). Mustard leaf extract was found to have protective effect against chromosomal damage and this was associated with modulation of lipid per- oxidation as well as an increase in GSH and GSH-dependent enzyme glutathione S-transferase (GST). These findings suggested that the intake of mustard leaf could lead to protection against in vivo genotoxicity and oxidative stress (Tiku et al. 2008). Mustard oil was found to have a protective role against atherogenic index (AI) and lipid peroxidation under both normal and stress conditions in rats (Benson and Devi 2009). Three kaempferol glycosides, kaempferol-3-O-(2-O-sinapoyl)-beta- d-glucopyranosyl-(1→2)-beta-d-glucopyranoside-7-O-beta-d-glucopyranoside (1), kaempferol-3-O-beta-d-glucopyranosyl-(1→2)-beta-d-glucopyranoside-7- O-beta-d-glucopyranosyl-(1→6)-beta-d-glucopyranoside (2), and kaempferol-3- O-(2-O-sinapoyl)-beta-d-glucopyranosyl-(1→2)-beta-d-glucopyranoside-7-O- beta-d-glucopyranosyl-(1→6)-beta-d-glucopyranoside (3), isolated from mustard

References 407 leaves, were tested for antioxidant activities by measuring the scavenging activities on DPPH and ONOO(−). Compounds 1 and 3 showed good antioxidant activities toward both DPPH and ONOO(−), while compound 2 showed only a weak activity toward ONOO(−) and no DPPH activity (Jung et al. 2009). Lee et al. (2010) found mustard leaf kimchi ethanolic extracts to exhibit a strong protective effect against lipid oxidation in raw ground pork. Mustard leaves were shown to have good scav- enging effect on DPPH radical with good phenolic content (Khattak 2011). A sus- pension of mustard seed extract was found to suppress oxidized-LDL-induced macrophage respiratory burst in vitro, to prevent growth, and to induce apoptotic death of SW480 cells (a human colon cancer cell line), while no such effects were found for normal 3T3 cells. A diet enriched with mustard seeds was shown to decrease plasma levels of the lipid peroxidation product malonaldehyde in mice exposed to the colon cancer-inducer azoxymethane (AOM). Such a diet also dose-dependently enhanced the activity of several antioxidant enzymes, such as superoxide dismutase (SOD), catalase, and GSH-peroxidase and, moreover, reduced AOM-mediated formation of colon adenomas by about 50% (Yuan et al. 2011). Sengupta and Ghosh (2012) reported that compared with native mustard oil, the capric acid-enriched mustard oil improved blood lipids, enhanced antioxidant protection, and reduced lipid peroxidation in male albino rats. Regulatory Status GRAS 182.10, GRAS 182.20 and GRAS 184.1527. Standard ISO 1237 (Specification), ISO 17059 (Oilseeds). References Benson MK, Devi K (2009) Influence of omega-6/omega-3 rich dietary oils on lipid profile and antioxidant enzymes in normal and stressed rats. Indian J Exp Biol 47:98–103 Bhattacharya A, Li Y, Wade KL, Paonessa JD, Fahey JW, Zhang Y (2010) Allyl isothiocyanate-rich mustard seed powder inhibits bladder cancer growth and muscle invasion. Carcinogenesis 31(12):2105–2110 Choi JS, Jung MJ, Park HJ, Chung HY, Kang SS (2002) Further isolation of peroxynitrite and 1,1-diphenyl-2-picrylhydrazyl radical scavenging isorhamnetin 7-O-glucoside from the leaves of Brassica juncea L. Arch Pharm Res 25:625–627

408 38 Mustard Gagandeep, Dhiman M, Mendiz E, Rao AR, Kale RK (2005) Chemopreventive effects of mustard (Brassica campestris) on chemically induced tumorigenesis in murine forestomach and uterine cervix. Hum Exp Toxicol 24:303–312 Gill SS, Khan NA, Tuteja N (2011) Differential cadmium stress tolerance in five Indian mustard (Brassica juncea L.) cultivars: an evaluation of the role of antioxidant machinery. Plant Signal Behav 6(2):293–300 Jung HA, Woo JJ, Jung MJ, Hwang GS, Choi JS (2009) Kaempferol glycosides with antioxidant activity from Brassica juncea. Arch Pharm Res 32:1379–1384 Khattak KF (2011) Nutrient composition, phenolic content and free radical scavenging activity of some uncommon vegetables of Pakistan. Pak J Pharm Sci 24:277–283 Kim JE, Jung MJ, Jung HA, Woo JJ, Cheigh HS, Chung HY, Choi JS (2002) A new kaempferol 7-O-triglucoside from the leaves of Brassica juncea L. Arch Pharm Res 25:621–624 Kim HY, Yokozawa T, Cho EJ, Cheigh HS, Choi JS, Chung HY (2003) In vitro and in vivo antioxi- dant effects of mustard leaf (Brassica juncea). Phytother Res 17:465–471 Lamy E, Garcia-Käufer M, Prinzhorn J, Mersch-Sundermann V (2012) Antigenotoxic action of isothiocyanate-containing mustard as determined by two cancer biomarkers in a human inter- vention trial. Eur J Cancer Prev 21(4):400–406 Lee MA, Choi JH, Choi YS, Han DJ, Kim HY, Shim SY, Chung HK, Kim CJ (2010) The antioxi- dative properties of mustard leaf (Brassica juncea) kimchi extracts on refrigerated raw ground pork meat against lipid oxidation. Meat Sci 84:498–504 Sengupta A, Ghosh M (2012) Comparison of native and capric acid-enriched mustard oil effects on oxidative stress and antioxidant protection in rats. Br J Nutr 107(6):845–849 Tiku AB, Abraham SK, Kale RK (2008) Protective effect of the cruciferous vegetable mustard leaf (Brassica campestris) against in vivo chromosomal damage and oxidative stress induced by gamma-radiation and genotoxic chemicals. Environ Mol Mutagen 49:335–342 Wang T, Liang H, Yuan Q (2011) Optimization of ultrasonic-stimulated solvent extraction of sini- grin from Indian mustard seed (Brassica Juncea L.) using response surface methodology. Phytochem Anal 22(3):205–213 Yokozawa T, Kim HY, Cho EJ, Choi JS, Chung HY (2002) Antioxidant effects of isorhamnetin 3,7-di-O-beta-D-glucopyranoside isolated from mustard leaf (Brassica juncea) in rats with streptozotocin-induced diabetes. J Agric Food Chem 50:5490–5495 Yokozawa T, Kim HY, Cho EJ, Yamabi N, Choi JS (2003) Protective effects of mustard leaf (Brassica juncea) against diabetic oxidative stress. J Nutr Sci Vitaminol (Tokyo) 49:87–93 Yuan H, Zhu M, Guo W, Jin L, Chen W, Brunk UT, Zhao M (2011) Mustard seeds (Sinapis Alba Linn) attenuate azoxymethane-induced colon carcinogenesis. Redox Rep 16(1):38–44

Chapter 39 Myrtle Botanical Name: Myrtus communis L. Synonyms: Corsican pepper, wax myrtle. Family: Myrtaceae. Common Names: French: Myrtle commun; German: Myrte; Spanish: Mirto; Italian: Mirto; Hindi: vilayatimehndi; Arabic: hadass. Introduction History Myrtle (Myrtus communis) is native to the Mediterranean region and is mainly cultivated for the extraction of its essential oil. Used in ancient Greece, the astrin- gent, tonic, and antiseptic properties of its leaves are used to heal wounds, or inter- nally to remedy disorders of the digestive and urinary systems. The oil is antiseptic and anti-catarrhal, and is used to treat chest ailments. Myrtle branches, berries, and leaves have been used since Biblical times. It is used in the Eastern Mediterranean islands of Sardinia, Corsica, and Crete and western Asia to flavor smoked or roasted meats. The myrtle was held as the emblem of honor and authority, and worn by the Athenian judges in the exercise of their functions. The wreaths of the Grecian and Roman victors, in the Olympian and other festivities, were made from myrtle leaves. It is alluded to in the Scriptures, and Jews used it as a token of peace, and entered into bridal decorations. In the Mohammedan tradition it was among the pure things car- ried by Adam out from the Garden of Eden. The leaves, berries, and twigs have been employed in flavoring food and wines, and the leaves are said to furnish a good tea. D.J. Charles, Antioxidant Properties of Spices, Herbs and Other Sources, 409 DOI 10.1007/978-1-4614-4310-0_39, © Springer Science+Business Media New York 2013

410 39 Myrtle Producing Regions Native to the Mediterranean region and western Asia. It is widely cultivated else- where, especially common in Morocco, Tunisia, and Algeria. Tunisia is the major supplier of the oil, with Spain, France, and Italy producing small quantities. Botanical Description An evergreen shrub or small tree, generally 3–7-m (9–25 ft) high. It has stiff branches and reddish twigs, with dark glossy green leaves. The attractive flowers are white or pinkish and very fragrant. Fruits are round, reddish-blue to violet ber- ries. The whole plant is very aromatic. Parts Used Myrtle seeds are purple black berries and used whole or coarsely ground. The leaves are used whole or chopped. Essential oil is obtained by steam distillation of the fresh leaves. The oil is yellow to greenish-yellow mobile liquid. Flavor and Aroma Leaves have refreshing, fragrant, and orange like aroma. Myrtle berries have sweet, with rosemary-like and juniper-like flavors. Has a strong camphoraceous-spicy, sweet-herbaceous top note. The middle note is fresh, sweet-herbaceous, camphora- ceous. The dry out is not at all tenacious. Active Constituents Essential oil (0.2–0.8%). The major constituents of the oil are myrtenol, myrtenyl acetate, a-pinene, 1,8-cineole, limonene, a-terpinyl acetate, and linalool. Myrtle is rich in volatile oils, phenolic acids such as gallic and ellagic acids, flavonoids, fatty acids, tannins, and anthocyanin pigments (Martin et al. 1990). Preparation and Consumption The leaves of myrtle are used in salads, stews, roast meats, and stuffings. They are also used to wrap roast pork or wild game before cooking. Italians wrap meats with myrtle branches and then roast, smoke, or broil them. The leaves are stuffed in

Antioxidant Properties 411 meats and removed before eating. The berries have been used to flavor wine and in desserts, sweet dishes, and liqueurs. The wood, leaves, and branches give the meats a very fragrant note. Medicinal Uses and Functional Properties Myrtle is antiseptic, astringent, and expectorant. Myrtle oil has been researched for normalizing hormonal imbalances of the thyroid and ovaries as well as balancing the hyperthyroid. Myrtle oil has many reported benefits for the skin such as helping with acne and oily skin. Research has also shown it to help the respiratory system with chronic coughs and tuberculosis. It is suitable to use for children’s coughs and chest complaints and may help support the immune function in fighting colds, flu, and infectious disease. Apply the oil topically, diffuse, or use in a humidifier. In folk medicine, myrtle has been used as anti-inflammatory drug. Myrtle is a culinary spice and flavoring agent for alcoholic beverages in the Mediterranean region. Myrtle has been shown to have antioxidant, anti-inflammatory, antimicrobial, insecticidal, and apoptotic activities (Conti et al. 2010; Mahboubi and Ghazian 2010; Sumbul et al. 2010; Djenane et al. 2011; Karaborklu et al. 2011; Amira et al. 2012). The tested materials (volatile oil, alcoholic and aqueous extracts, myricetin 3-O-b-glucopyranoside, myricetin 3-O-a-rhamnopyranoside, and gallic acid) of myrtle were found to have significant antihyperglycemic, anti-inflammatory, and antinociceptive effects as compared with control groups and reference drugs (Nassar et al. 2010). The extracts of myrtle exhibited antinociceptive activity against acetic acid-induced writhing and also showed significant activity against acute inflammation which was dose dependent for aqueous extracts. The ethanolic (0.05 g kg−1) and aqueous extracts (0.005, 0.015, and 0.03 g kg−1) demonstrated anti-inflammatory effects against chronic inflammation. The aqueous and ethanolic extracts of the aerial parts of Myrtus communis L. showed antinociceptive effects and these may be mediated by opioid receptors (Hosseinzadeh et al. 2011). The essential oil of Myrtus communis reduced leukocyte migration to the damaged tissue and exhibited anti- inflammatory activity. The oil also inhibited cotton pellet-induced granuloma and serum TNF-alpha and IL-6 in mice (Maxia et al. 2011). Antioxidant Properties Myrtle has been shown to possess antioxidant, antibacterial, and antifungal activi- ties (Vacca et al. 2003; Romani et al. 2004; Hayder et al. 2004; Montoro et al. 2006; Sepici-Dincel et al. 2007; Sacchetti et al. 2007; Sanjust et al. 2008; Yoshimura et al. 2008; Aidi Wannes et al. 2010; Mimica-Dukic et al. 2010; Serce et al. 2010; Kiralan et al. 2012; Messaoud and Boussaid 2011; Mothana et al. 2011; Amira et al. 2012). Semimyrtucommulone from myrtle was found to be a novel dietary antioxidant lead (Rosa et al. 2003). Myrtucommulone A and semimyrtucommulone from myrtle

412 39 Myrtle showed powerful antioxidant properties, protecting linoleic acid against free radical attack in simple in vitro systems, inhibiting its autoxidation and its FeCl3- and EDTA-mediated oxidation. Two industrial red myrtle liqueurs showed antioxidant capacity values comparable to those of red wine, expressed as mM of Trolox (Vacca et al. 2003). Hydroalcoholic extracts, ethylacetate extract, and aqueous residues after liquid–liquid extraction exhibited dose-dependent inhibition of oxidation induced by copper ions, and also reduced the formation of conjugated dienes (Romani et al. 2004). Hayder et al. (2004) found an aqueous extract, total flavonoids oligomer fraction (TOF), hexane, chloroform, ethyl acetate and methanol extracts, and essential oil from myrtle leaves to significantly decrease the SOS response induced by AFB1 (10 mg/assay) and Nifuroxazide (20 mg/assay). The aqueous extract, the TOF, and the ethyl acetate and methanol extracts also showed free radi- cal scavenging activity towards the DPPH radical. Myricetin-3-o-galactoside and myricetin-3-o-rhamnoside from myrtle leaves inhibited xanthine oxidase activity, lipid peroxidation, and scavenged the free radical DPPH. They induced an inhibitory activity against nifuroxazide, aflatoxin B1, and H2O2 induced mutagenicity. Moreover, these two compounds from myrtle leaves modulated the expression patterns of cellular genes involved in oxidative stress, in DNA damage repair, and in apoptosis (Hayder et al. 2008). The compounds myrtucommulone A and semi- myrtucommulone from myrtle were found to be great dietary antioxidants during the thermal, solvent-free degradation of cholesterol, and also significantly preserved LDL from oxidative damage induced by Cu2+ ions at 2 h of oxidation (Rosa et al. 2008). Amensour et al. (2009) studied the total phenolic content and antioxidant activity of the methanolic, ethanolic, and aqueous extracts of myrtle leaves and ber- ries. Overall the leaf extracts had higher total phenol content and showed higher antioxidant activities than the berry extracts. They also found a positive correlation between the phenolic content and antioxidant activity. The methanol extracts of dif- ferent myrtle plant parts (leaf, flower, and stem) showed better antioxidant activity than the leaf and flower essential oils (Aidi Wannes et al. 2010). Regulatory Status Food additive. FDA 121.1163. References Aidi Wannes W, Mhamdi B, Sriti J, Ben Jemia M, Ouchikh O, Hamdaoui G, Kchouk ME, Marzouk B (2010) Antioxidant activities of the essential oils and methanol extracts from myrtle (Myrtus communis var. italica L.) leaf, stem and flower. Food Chem Toxicol 48(5):1362–1370 Amensour M, Sendra E, Abrini J, Bouhdid S, Perez-Alvarez JA, Fernandez-Lopez J (2009) Total phenolic content and antioxidant activity of myrtle (Myrtus communis) extracts. Nat Prod Commun 4(6):819–824